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302-79-4 Usage

Biological Activity

Endogenous agonist for retinoic acid receptors. Also positively modulates PPAR δ receptors (K d = 17 nM). Promotes differentiation of embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro .

Originator

Aberel,McNeil,US,1973

Fire Hazard

Flash point data for Tretinoin are not available; however, Tretinoin is probably combustible.

Warnings and Precautions

Patients who are allergic to this drug or vitamin A derivatives, have acute or subacute dermatitis, have eczema or related skin diseases, and pregnant women should not use this drug. Use with caution if susceptible to allergies. Breastfeeding women should stop breastfeeding when using this drug, and women of childbearing age should not get pregnant when using this drug. Children should use with caution. Keep drug out of eyes and other mucosa (such as mouth and nose). Not suitable or skin folds and skin ulcerations. If the applied area experiences burning sensation, itching, or redness and swelling, stop use immediately, clean the applied area, and consult a physician if necessary. This drug is used to treat acne, and a couple weeks of use can prevent worsening, while continued use for over 6 weeks will have the best curative effect. This drug is not suitable use in large areas, and daily dosage should not exceed 20g. While using this drug, do not use any drugs, cosmetics, or cleansers that may irritate and damage the skin to prevent worsened skin reactions and adverse effect caused by increased drug absorption. Sunlight can increase retinoic acid’s irritation to skin and break down retinoic acid. Animal studies showed that retinoic acid can increase the carcinogenic ability of ultraviolet rays, so this drug is best used at night and before sleep. Avoid direct sunlight during treatment, or protect treated areas from sunlight.

Clinical Use

The major toxic effect of tretinoin is erythema and irritation of the skin to which it is applied, especially if the skin is moist.This toxicity often decreases with continued therapy.

World Health Organization (WHO)

Tretinoin, a retinol derivative, was introduced in 1973 exclusively for the topical treatment of severe acne. Preparations of tretinoin are indicated for topical use only since oral administration has been associated with risk of toxicity from hypervitaminosis-A and subsequently of teratogenicity.

Pharmacokinetics

A small amount is absorbed by the skin through external use, and absorption increases as application area increases. Approximately 5% of the externally applied amount is excreted through urine. This product is well-absorbed when taken orally and reaches peak blood concentration in 3 hours. With an oral dosage of 1mg/kg, blood concentration can reach 0.3-0.5 mg/ml. After oral absorption, it will bind universally with serum protein, and its average clearing half-life is 0.7 hours. After a single 40mg dose, blood concentration reaches its endogenous metabolism level in about 7-12 hours. Multiple oral doses do not appear to accumulate in the body, but blood concentration will noticeably decrease, possibly due to the induction of cytochrome P450, thus causing the clearing rate to increase and bioavailability to decrease. It is mainly metabolized in the liver, and its metabolite is esterified glucuronic acid. 60% of the drug is excreted by the kidneys, it can also be excreted through bile, and its metabolite’s half-life is longer than that of the drug itself.

General Description

Tretinoin is available in 10-mg capsules for oral administrationin the treatment of APL. The mechanism of action involvespassive diffusion through the cell membrane andthen movement to the nucleus where it interacts with theretinoic acid receptor (RAR) portion of the PML-RAR fusionprotein. Binding of tretinoin allows the cell to differentiateand has also been shown to result in the destruction ofthe PML-RAR fusion protein. Resistance to tretinoin isproblematic and associated with an increase in cellularretinoic acid–binding proteins (CRAPBs) located in the cytosol.The complexation with tretinoin prevents movementinto the nucleus and may present the drug to metabolizingenzymes that inactivate it. Amino acid mutation of thePML-RAR protein has also been established as a mechanismof resistance. The agent is well absorbed upon oral administrationand highly (95%) protein bound. Metabolismoccurs in the liver and several inactive metabolites havebeen identified including 13-cis-retinoic acid, 4-oxo cisretinoic,4-oxo trans-retinoic acid and 4-oxo trans-retinoicacid glucuronide. Elimination occurs in the urine (63%) andfeces (31%) with an elimination half-life of 40 to 120 minutes.Vitamin A toxicity is seen in nearly all patients andpresents as headache, fever, dryness of the skin, skin rash,mucositis, and peripheral edema. APL differentiation syndromesuch as that seen for arsenic trioxide also occurs.Cardiovascular effects include flushing, hypotension, CHF,stroke, and myocardial infarction have been reported butoccur only rarely. There are also several CNS and GI effectsthat have been associated with the agent as well.

Physicochemical property

Retinoic acid is a yellow needle crystal, with a similar smell of vitamin acetate. Soluble in methanol, ethanol, acetone, chloroform, dichloromethane , also in vegetable oil and fatty. In case of light, it is thermal instability, suck up moisture in the air, polymerization and metamorphism in water. The melting point of all trans-vitamin A acid is 182~180°C, the melting range of which is mixed with a small amount of isomers is 170~190°C. Tretinoin structure

Adverse reaction

This product may cause skin irritation symptoms such as burning, erythema, swelling, desquamation, crusting, pigment increase or decrease, may make the skin lesions more obvious, but also showed that the drug is working, not aggravated illness. Most of the skin can be adapted and tolerated, the phenomenon can be gradually disappeared. If irritation persists or increased, you can take intermittent or suspended medication.

Manufacturing Process

100 parts of beta-ionol are dissolved in 200 parts of dimethylforrnamide and after the addition of 165 parts of triphenylphosphine hydrobromide, stirred for 7 hours at room temperature. Then 70 parts of 4-methyl-1-al-hexadiene- (2,4)-acid-(6) (melting point 177°C, white needles from water) are added to the now clear solution. 150 parts of isopropanol are added and the whole cooled to -30°C. Into this solution, while stirring vigorously, 190 parts by volume of a 30% solution of sodium methylate in methanol are allowed to flow in. A vigorous exothermic reaction takes place and the temperature in the interior of the flask rises to +5°C. It is stirred for another 5 minutes and neutralized with 10% of sulfuric acid (until acid to Congo). After stirring for 2 hours at room temperature, the mass of vitamin A acid has crystallized out. It is sharply filtered off by suction and washed with a little ice-cold isopropanol. From the filtrate, a further small amount of mainly all trans vitamin A acid crystallizes out upon the addition of water. The filter cake is suspended in 600 parts of water and stirred for 4 hours at room temperature; it is filtered by suction and the product washed with water. It is dried in vacuo at 40° to 50°C and 115 parts of vitamin A acid are obtained. The melting point lies between 146° and 159°C. The mixture of the all trans and mainly 9,10-cis vitamin A acid may be separated by fractional crystallization from ethanol. All trans vitamin A acid has a melting point of 180° to 182°C and 9,10-cis vitamin A acid, which crystallized in the form of pale yellow fine needles collected into clusters, has a melting point of 189° to 190°C.

Veterinary Drugs and Treatments

Topical tretinoin may be useful in treating localized follicular or hyperkeratotic disorders such as acanthosis nigrans, idiopathic nasal and footpad hyperkeratosis, callous pyodermas, or chin acne. Tretinoin’s exact mechanism of action is not well understood, but it stimulates cellular mitotic activity, increases cell turnover, and decreases the cohesiveness of follicular epithelial cells.

Uses

Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation

Clinical application

Retinoic acid is mainly used in the treatment of psoriasis, ichthyosis, follicular keratosis, acne, lichen planus, verrucous epidermal nevus, impetigo, vitiligo, lichen psoriasis, the face of pityriasis alba, etc. In addition, the drugs also have some preventive effect on skin cancer. Tretinoin Cream

Drug interaction

(1)Retinoic acid combining with light sensitive drugs can increase the risk of photosensitiveness. (2)Retinoic acid combining with soap and detergents, containing keratolytic agents (such as peroxy benzoic acid, Resorcinol, salicylic acid, sulfur,etc), ethanol preparation, isotretinoin can aggravate irritation or dryness to skin, and therefore must be used with caution. (3) Retinoic acid combining with sago cimetidine, cyclosporine and diltiazem, verapamil and ketoconazole, can cause an increase in the blood concentration of the drug, and may lead to retinoic acid poisoning. (4 Retinoic acid combining with pentobarbital, rifampicin, phenobarbital, can cause the blood concentration of the product decreasing. (5) The product will affect the liver cytochrome P450 enzyme system, resulting in changes in blood concentrations of the drug. (6)Taking drugs oryzanol, vitamin B1, vitamin B6 with Tretinoin, can make headache relieved or disappeared, because of adverse reactions of the drug. There are Informations on Common tretinoin in the Department of Dermatology,incluing the pharmacological effects , pharmacokinetics, pharmacodynamics, indications, drug interactions, and adverse reaction of the drug, these were edited by Yuri Huang in the chemcialbook (2015-09-24).

Mechanisms of Action

Retinoic acid mainly affects bone growth and epithelium metabolism, it can promote epithelium cell growth and renewal, and it can inhibit keratinocyte growth and differentiation to correct hyperkeratosis. Thus, it has certain curative effects on diseases related to keratinization, hypokeratinization and hyperkeratinization. A localized application can penetrate the skin very quickly and cause significant growth in epithelial cells. Retinoic acid has a strong and rapid inhibiting effect on sebaceous glands and can reduce sebum secretion. Retinoic acid promotes epidermal growth, thickens the stratum granulosum and stratum spinosum, and affects K1 and K10 keratinysis in late stage epidermal cell differentiation to influence the siloxin to silymeric protein process and cross-linked coating formation, thus promoting epidermal granulosa cells to differentiate towards the cuticle layer. It regulates follicular sebaceous gland epithelium keratinization abnormalities to remove keratin plugs, thus being able to prevent and remove acne lesions, and follicular epithelial renewal can also prevent keratin plugs and acne formation. In addition, retinoic acid can also affect melanogenesis of melanocytes with a multi-site effect, and it can inhibit the activity of tyrosine hydroxylase, dopa oxidase, dihydroxyl indole oxidase, and other type-three catalytic enzymes, thus lowering the formation of melanin and reducing hyperpigmentation. It has not impact on normal human melanocyte tyrosinase activity and melanin content.

Definition

ChEBI: A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.

Vitamin A acid medicine

Vitamin A acid medicine is a kind of natural or synthetic existence with vitamin A activity of retinol (retinol) derivatives. The drug discovery is regarded as a new milepost for treatment of skin diseases and cosmetic pharmacology. In the last 20 years, the application of the dimension A acid has made great progress in the treatment of many skin diseases. So far, there have been 2500 retinoic acid derivatives. According to its development process and chemical structure, they can be divided into three generations: the first generation is class of non aromatic retinoid, tretinoin and isotretinoin as the representative. The second generation is class of single aromatic A acids, etretinate and acitretin as the representative; the third generation is class of aromatic dimensional A acid, aromatic methyl ethyl acetylene, adapalene and vitamin A acid ethyl ester as the represented. use of of vitamin A in skin diseases

The indications

Used in the treatment of acne vulgaris, especially the blackhead acne lesions, senile, fluorescent or drug skin atrophy, ichthyosis and various abnormal keratinization and pigment excessive calm skin disease, and psoriasis.

Uses

antipruritic

Uses

retinoic acid (tretinoin) is a vitamin A derivative. It has demonstrated an ability to alter collagen synthesis, increase dermal hyaluronic acid levels, and stimulate fibroblast growth and the extracellular matrix. It is used for keratinization disorders and for treating acne. Retinoic acid’s anti-aging effect has been convincingly documented and it is often used for treating the visible signs of aging, though these results can take approximately 6 months to be visible. It is associated with a number of adverse effects, including irritation, photosensitivity, skin dryness, redness, and peeling. It should also not be used while pregnant.

Pharmacodynamics

Tretinoin can increase the cell nucleus division and epidermal cell turnover, form of the stratum corneum cell adhesion, and easy to fall off. It can remove the existing acne, while inhibiting the formation of new acne, hair follicle epithelial replacement can prevent the blockage of the plug. The synthesis of keratin is also inhibited, which can affect the metabolism of epithelial cells. It has the effect of promoting the proliferation and differentiation of epithelial cells, and the dissolution of keratinocytes.

Purification Methods

Purify the acid by chromatography on silicic acid columns, and eluting it with a small amount of EtOH in hexane. Also dissolve it in Et2O, wash it with H2O, dry (Na2SO4), evaporate and the solid residue is recrystallised from MeOH (0.53g /3.5mL MeOH to give 0.14g) or EtOH. It also recrystallises from i-PrOH, or as the methyl ester from MeOH. UV in MeOH has max at 351nm ( 45,000). 9-Cis-acid forms yellow needles from EtOH, with m 189-190o, and its UV in MeOH has max at 343nm ( 36,500); the 13-cis-acid forms red-orange plates from i-PrOH with m 174-175o, and UV has max at 345nm ( 39,800). Store it in the dark, in an inert atmosphere, at 0o [Robeson et al. J Am Chem Soc 77 4111 1955]. [Beilstein 9 IV 2387.]

Drug Interactions

Combined use with light-sensitive drugs may increase the risk of light sensitivity. Use with caution when combined with soap and other detergents, preparations containing keratolytic (such as benzoyl peroxide, thalidomide, salicylic acid, and sulfur), preparations containing ethanol, or isotretinoin, as this may worsen skin irritation and dryness. Combined use with cimetidine, cyclosporine, diltiazem, verapamil and ketoconazole may increase the blood concentration of this drug and lead to retinoic acid poisoning. Combined use with pentobarbital, phenobarbital and rifampicin may decrease the blood concentration of this drug. This drug will impact the hepatic cytochrome P450 enzyme system and change the blood concentration of this drug. Taking oryzanol, vitamin B1 or vitamin B6 while also taking this drug may alleviate or eliminate adverse effects of this drug, including headaches.

Usage dosage

(1) ointment: use 0.1% ointment for the other skin lesions and 0.05% ointment for acne skin lesions in the topical application. Clean the skin with warm water after one time every night. (2) gel: apply to the affected area. At the beginning of treatment , it can be taken one time every two days or every three days. Afterwards smear one time every night.

Indications

Topical tretinoin (Retin-A, Renova, Avita), like isotretinoin, alters keratinization in the acroinfundibulum. In addition, it reverses certain premalignant and other histological changes associated with the photoaging changes that accompany chronic exposure to ultraviolet radiation. Topically applied tretinoin is indicated in comedogenic and papulopustular acne vulgaris, and its mild exfoliative effects make it sometimes useful in molluscum contagiosum, flat warts, and some ichthyotic disorders. It is often prescribed to lessen the clinical signs of photoaging (wrinkling and hyperpigmented macules).

Chemical Properties

Yellow-Orange Powder

Reactivity Profile

Tretinoin may discolor on exposure to light. Tretinoin is extremely sensitive to exposure to light and, therefore, Tretinoin should be fully protected from light during all handling. Solutions are unstable in the presence of strong oxidizers. Tretinoin is incompatible with strong oxidizing agents. .

General Description

Yellow to light-orange crystalline powder.

Adverse reactions

May cause skin irritations such as a burning sensation, erythema, swelling, desquamation, scabbing, or change in pigmentation. May cause skin lesions to become more obvious, but this means that the drug is taking effect, and not that the condition is worsening. Mostly tolerated or tolerable on the skin, and irritation may subside gradually. If irritation continues or worsens, use periodically or cease use.

Brand name

A-acido;Acid a vit;Acnavit;Acnavyse;Acretin;Airoderm;Aknebon;Aknefug;Anition;Antibio-aberel;Apsor;A-vitamisyre;Avitoin;Cordes vas;Dermoclar;Dermojuventas;Derugin;Locacid;Pigmanorm;R0 22-6595;Reiderma;Retin a;Ro 1-5488;Sebo-psor;Stie vaa;Stievaa;Tretin m;Vas dexa;Verra-med;Vitacid a.

Therapeutic Function

Keratolytic

Uses

keratolytic, antiacne, antineoplastic

Indications and Usage

Retinoic acid is a commonly used dermatological drug and an intermediate product in bodily vitamin A (dimethyl alcohol) metabolism. It has a similar odor to that of vitamin A acetate. It is easily soluble in methanol, ethanol, acetone, chloroform, dichloromethane, and it is also soluble in vegetable oil and fats. It is instable when in contact with light and heat, hygroscopic in air, and polymerizes and metamorphosizes when in contact with water. Retinoic acid also anti-tumor, wound-healing, and infection-resisting effects. It is mainly used clinically to treat psoriasis, hair follicle keratosis, acne, lichen planus, verrucous epidermis nevus, ureophora, vitiligo, pityriasis rosea, and facial pityriasis simplex, especially blackhead skin lesions, and senile, sun-induced, or drug induced skin atrophy, as well as various keratosis abnormalities and hyperpigmentation diseases. In addition, it also has certain preventative effects against skin cancer. Retinoic acid can significantly inhibit experimental acne breakouts.

Uses

(1) Applies to abnormal tyshiyongyupe of acne, fish phosphorus disease and abnormal psoriasis. (2) Resistance to abnormal skin drugs. (3) Tretinoin mainly affects the growth of bones and epithelial metabolism, can promote epithelial cell proliferation and updates, and can inhibit the proliferation and differentiation of keratinocytes, so hyperkeratosis can be back to normal. Therefore many complete or incomplete keratosis, hyperkeratosis of diseases have a certain therapeutic effect, treat a variety of skin diseases. Tretinoin is mainly used in the treatment of psoriasis, ichthyosis, follicular keratosis, acne, lichen planus, verrucous epidermal nevus, impetigo, vitiligo, lichen psoriasis, the face of pityriasis alba, etc.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic and teratogenic data. Human mutation data reported. A human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. Used to treat acne and other skin problems.

Pharmacokinetics

External use has a small amount of skin absorption, large area of application of the increase in absorption. About 5% of the amount of external use urine. This product is absorbed well, the blood can reach the concentration peak after 3 hours, blood concentration can reach 0.3~0.5mg/ml, after oral administration of 1 mg/kg. After oral absorption, it is widely combination with plasma protein and has half-life of 0.7 h in a mean elimination. After a single oral dose of 40mg, blood drug concentration can be up to the source metabolic level in 7~12 hours. Multiple oral administration has not seen in vivo accumulation, but the blood concentration of the drug is significantly decreased, which may be due to the induction of cytochrome P450 enzymes, and the elimination of the rate of increase and bioavailability. It mainly used in the liver metabolism, which is metabolites of glucose acid esters. 60% of metabolites is by renal excretion, and can also be excreted by bile but metabolite half-life is longer.

Dermatology drugs

Retinoic acid(Tretinoin) is commonly used in dermatology drugs, which is the department of vitamin A (Victoria methanol) metabolic intermediates.It mainly affects the growth of bones and epithelial metabolism, can promote epithelial cell proliferation and updates, and can inhibit the proliferation and differentiation of keratinocytes, so hyperkeratosis can be back to normal. Therefore many complete or incomplete keratosis, hyperkeratosis of diseases have a certain therapeutic effect, treat a variety of skin diseases. The use of the drug can penetrate topical skin quickly, enable significantly increased epithelial cell turnover. This class of drugs has strong and rapid inhibition on the secretion of the sebaceous glands, can reduce sebum secretion. In addition, the product also has anti-tumor, promote wound healing and anti-inflammatory effects.

Air & Water Reactions

Tretinoin may be sensitive to prolonged exposure to air. Insoluble in water.

Pharmacological action

Retinoic acid can induce epidermal hyperplasia, and improve the granular layer and the cell layer thickness.It can influence the silk protein process and the formation of cross-linked film and promote the differentiation of epidermal granular layer cells in the late stage of the differentiation of the epidermal cells by affecting K10, K1 keratin solution. This product can significantly inhibit the formation of experimental acne, prevent and eliminate acne lesions. Tretinoin also affect melanocyte cell melanogenesis , it has more than a number of functional points, having inhibitory effect on the activity of Tyrosine hydroxylase, dopa oxidase and two hydroxyindole oxidase three catalyzing enzyme, so as to reduce the formation of melanin, reduce skin pigmentation. It has no effect on the normal black prime cellular tyrosinase activity and black pigment composition.

Precautions

(1) This drug is contraindicated in pregnant women and patients with the allergic to the Tretinoin, the A derivative of vitamin A, acute or subacute dermatitis, eczema, skin diseases. (2) Allergic caution. (3) Women should stop breastfeeding during the period of the nursing period. Women of childbearing age are prohibited during the period of pregnancy .Children with caution. (4) The product should avoid contacting with eyes and other mucous membranes (e.g., mouth, nose, etc.). Do not use in skin of wrinkling location and skin ulceration. (5) The site of using medicine, appearing the things such as burning, itching, redness, etc. should discontinue medication, and the local is washed clearly. Consult the doctor if necessary. (6) For the treatment of acne, the first few weeks ache can be temporarily intensified, but should continue to treat more than 6 weeks to reach the maximum effect. (7) The product should not be used in large areas, the daily dosage should not exceed 20g. (8) During the course of medication, do not use other drugs ,which can cause irritation and damage to skin, cosmetics and cleaning agents, so as not to aggravate the skin reaction, resulting in increase in drug absorption and cause systemic adverse reactions. (9) The sun can accelerate Tretinoin decomposition and stimulate heavier to the skin. Animal experiments suggest that Tretinoin can enhance the ability of ultraviolet radiation, so the product is most appropriate in the evening and bedtime application, the treatment process should avoid the sun, or the use of shading measures.
InChI:InChI=1/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1/b9-6+,12-11+,15-8+,16-14+

302-79-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (R0064)  Retinoic Acid  >98.0%(T) 302-79-4 1g 690.00CNY Detail
TCI America (R0064)  Retinoic Acid  >98.0%(T) 302-79-4 5g 2,390.00CNY Detail
Alfa Aesar (44540)  Retinoic acid, 98%    302-79-4 0.1g 207.0CNY Detail
Alfa Aesar (44540)  Retinoic acid, 98%    302-79-4 0.5g 547.0CNY Detail
Alfa Aesar (44540)  Retinoic acid, 98%    302-79-4 2g 1810.0CNY Detail
Sigma-Aldrich (PHR1187)  Tretinoin  pharmaceutical secondary standard; traceable to USP and PhEur 302-79-4 PHR1187-3X100MG 1,024.57CNY Detail
Sigma-Aldrich (T1850000)  Tretinoin  European Pharmacopoeia (EP) Reference Standard 302-79-4 T1850000 1,880.19CNY Detail
USP (1674004)  Tretinoin  United States Pharmacopeia (USP) Reference Standard 302-79-4 1674004-5X30MG 4,662.45CNY Detail
Sigma (R2625)  Retinoic acid  ≥98% (HPLC), powder 302-79-4 R2625-50MG 245.70CNY Detail
Sigma (R2625)  Retinoic acid  ≥98% (HPLC), powder 302-79-4 R2625-100MG 343.98CNY Detail
Sigma (R2625)  Retinoic acid  ≥98% (HPLC), powder 302-79-4 R2625-500MG 930.15CNY Detail
Sigma (R2625)  Retinoic acid  ≥98% (HPLC), powder 302-79-4 R2625-1G 1,676.61CNY Detail

302-79-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name all-trans-retinoic acid

1.2 Other means of identification

Product number -
Other names (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:302-79-4 SDS

302-79-4Synthetic route

ethyl (all-E)-retinoate
3899-20-5

ethyl (all-E)-retinoate

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 50℃; for 0.5h;98%
With potassium hydroxide In ethanol83%
With potassium hydroxide In ethanol at 50℃;83%
With potassium hydroxide In ethanol for 0.166667h; Heating;71%
RETINOL
68-26-8

RETINOL

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride; oxygen; bis-(3-methyl-1-imidazolyl)ethylene tetrafluoroborate In hexane at 50℃; under 760.051 Torr; for 3h; Reagent/catalyst; Darkness;90.2%
Multi-step reaction with 2 steps
1: MnO2 / CH2Cl2 / 2 h / Ambient temperature
2: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / MnO2 / CH2Cl2 / Ambient temperature
2: AgO / CNNa / methanol
View Scheme
(6R,7R)-3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
370578-75-9

(6R,7R)-3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

A

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

B

(R)-2-[(R)-Carboxy-(2-phenoxy-acetylamino)-methyl]-5-methylene-1-oxo-1,2,5,6-tetrahydro-1λ4-[1,3]thiazine-4-carboxylic acid

(R)-2-[(R)-Carboxy-(2-phenoxy-acetylamino)-methyl]-5-methylene-1-oxo-1,2,5,6-tetrahydro-1λ4-[1,3]thiazine-4-carboxylic acid

Conditions
ConditionsYield
With β-lactamase from Staphylococcus aureus 95; deuterated phosphate buffer In dimethylsulfoxide-d6 at 25℃; pH=7.2;A n/a
B 86%
trans-β-formyl crotonic acid
54168-84-2

trans-β-formyl crotonic acid

[3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride

[3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Stage #1: trans-β-formyl crotonic acid; [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere;
Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7 - 8; pH-value; Reagent/catalyst; Temperature;
85.3%
trans-β-formyl crotonic acid
54168-84-2

trans-β-formyl crotonic acid

[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride
53282-28-3

[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Stage #1: trans-β-formyl crotonic acid; [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere;
Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7-8; Reagent/catalyst; Temperature; pH-value; Inert atmosphere;
85.3%
all-trans-Retinal
116-31-4

all-trans-Retinal

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With silver(II) oxide; sodium cyanide In methanol for 18h; Ambient temperature;80%
With sodium cyanide; silver(l) oxide80%
With silver(II) oxide; sodium cyanide In methanol Yield given;
Conditions
ConditionsYield
With potassium hydroxide In ethanol for 0.5h; Heating; Yield given;A n/a
B 77%
With potassium hydroxide In ethanol for 0.5h; Heating; Yields of byproduct given;A n/a
B 77%
(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid
220212-06-6

(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

tributyl[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl)buta-1,3-dienyl]stannane

tributyl[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl)buta-1,3-dienyl]stannane

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
[PdCl2(NCMe)2] In N,N-dimethyl-formamide at 25℃; for 3h; Stille cross-coupling reaction;73%
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
20013-34-7

acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With pyridine In dichloromethane67%
5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene
38987-91-6

5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene

(E)-4-bromo-3-methyl-2-butenoic acid
19041-16-8

(E)-4-bromo-3-methyl-2-butenoic acid

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Stage #1: 5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene With potassium tert-butylate In tetrahydrofuran at -20℃; for 0.5h;
Stage #2: (E)-4-bromo-3-methyl-2-butenoic acid In tetrahydrofuran at -20 - 60℃; for 4h; Julia olefination;
65%
β-ionone
105593-28-0

β-ionone

methylmagnesium bromide
75-16-1

methylmagnesium bromide

dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate
419550-09-7

dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate

A

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

B

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Multistep reaction.;A 12%
B 61%
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
20013-34-7

acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique

A

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

B

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 20h;A n/a
B 60%
With barium dihydroxide In benzene for 0.5h;
aqueous potassium hydroxide

aqueous potassium hydroxide

aqueous sodium chlorite

aqueous sodium chlorite

2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

all-trans-Retinal
116-31-4

all-trans-Retinal

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With phosphoric acid In 1,4-dioxane; ethanol; hexane55.9%
[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Stage #1: [(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride With sodium methylate In methanol at -7.5℃; for 1h; Wittig Reaction;
Stage #2: With methanol; sodium hydroxide; ethanol; water at 20℃; Heating / reflux;
Stage #3: With water; acetic acid In dichloromethane
46%
Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;A 38%
B n/a
retinoyl fluoride
83802-77-1

retinoyl fluoride

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With water In isopropyl alcohol for 23h;38%
(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester
1620084-74-3

(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

methyl iodide
74-88-4

methyl iodide

A

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

C

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Stage #1: (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester; methyl iodide With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tris-(o-tolyl)phosphine In water; N,N-dimethyl-formamide at 60℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: With potassium hydroxide In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.0333333h; Inert atmosphere; Schlenk technique;
Stage #3: With formic acid In methanol; water; N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;
A 10%
B 0.5%
C 32%
trans-β-formyl crotonic acid
54168-84-2

trans-β-formyl crotonic acid

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol
59057-30-6

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With triphenylphosphine
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal
3917-41-7

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With potassium amide
(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-ethyl ester
115207-29-9

(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-ethyl ester

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With iodine; Petroleum ether Behandeln des erhaltenen all-trans-Retinsaeure-aethylesters mit wss.-aethanol. Kalilauge unter Stickstoff bei Lichtausschluss;
(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-methyl ester

(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-methyl ester

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With oxalic acid unter vermindertem Druck und Behandeln mit methanol. oder aethanol. Kalilauge;
With toluene-4-sulfonic acid; benzene Behandeln mit methanol. oder aethanol. Kalilauge;
With phenyl isocyanate at 110℃; Behandeln mit methanol. oder aethanol. Kalilauge;
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid
302-79-4, 3555-80-4, 4759-48-2, 5300-03-8, 5352-74-9, 68070-34-8, 68070-35-9, 97950-17-9, 98462-64-7, 124510-04-9

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With iodine
methyl 5-benzenesulphonyl-3.7-dimethyl-9-(2'.6'.6'.trimethyl-cyclohexen-1'-yl)-2.6.8-nonatrienoate
41551-56-8, 78088-24-1, 78088-25-2, 78088-26-3

methyl 5-benzenesulphonyl-3.7-dimethyl-9-(2'.6'.6'.trimethyl-cyclohexen-1'-yl)-2.6.8-nonatrienoate

A

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

B

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 2.5h; Heating; Yield given. Yields of byproduct given;
8-<2-(methylthio)-1,3-dithian-2-yl>-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)octa-1E,3E,5E,7E-tetraene
146558-55-6

8-<2-(methylthio)-1,3-dithian-2-yl>-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)octa-1E,3E,5E,7E-tetraene

A

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

B

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
(2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid
131189-98-5, 131235-62-6

(2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With iodine; toluene-4-sulfonic acid 1.) methylene dichloride, reflux; 2.) diethyl ether/benzene, rt, 7 h; Yield given;
Multi-step reaction with 2 steps
1: 95 percent / p-toluenesulfonic acid / CH2Cl2 / Heating
2: I2
View Scheme
(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene
73395-75-2

(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene

(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid
220212-06-6

(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

methyl iodide
74-88-4

methyl iodide

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
Yield given. Multistep reaction;
all-trans-Retinal
116-31-4

all-trans-Retinal

A

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

B

4-hydroxy-all-trans-retinal
18344-42-8

4-hydroxy-all-trans-retinal

Conditions
ConditionsYield
With rabbit liver microsomal P450 1A1 isozyme; NADPH; NADPH-cytochrome P450 reductase In phosphate buffer at 30℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reaction partners; Oxidation; Enzymatic reaction;
trans-β-formyl crotonic acid
54168-84-2

trans-β-formyl crotonic acid

3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol

3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With triphenylphosphine
4t-<2,6,6-trimethyl-cyclohex-1-enyl>-but-3-en-2-ol

4t-<2,6,6-trimethyl-cyclohex-1-enyl>-but-3-en-2-ol

3-methyl-6-oxo-hexa-2t,4t-dienoic acid

3-methyl-6-oxo-hexa-2t,4t-dienoic acid

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With triphenylphosphine
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

all-trans-methyl retinoate
339-16-2

all-trans-methyl retinoate

Conditions
ConditionsYield
In methanol; hexane; benzene at 20℃; for 0.75h;100%
With methanol In benzene at 20℃; Methylation;
1-Hexadecanol
36653-82-4

1-Hexadecanol

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

retinyl palmitate
136013-95-1

retinyl palmitate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 24h; optical yield given as %de;99%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

C20H38O2

C20H38O2

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr;99%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-(all-trans-Retinoyl)-imidazole
61319-45-7

N-(all-trans-Retinoyl)-imidazole

Conditions
ConditionsYield
In acetonitrile for 1h; Heating;98.6%
In N,N-dimethyl-formamide Ambient temperature;80%
In benzene at 20℃; for 1h;60%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

3-(tert-butyldisulfanyl)propane-1,2-diol
131111-38-1

3-(tert-butyldisulfanyl)propane-1,2-diol

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2-tert-butyldisulfanyl-1-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-ethyl ester
131111-41-6

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2-tert-butyldisulfanyl-1-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 12h; Ambient temperature;98%
Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2,2-dimethyl-propionyloxymethyl ester

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 3h; Alkylation;98%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

vanillylamine hydrochloride
7149-10-2

vanillylamine hydrochloride

Retvanil

Retvanil

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In tetrahydrofuran98%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(+)-octan-2-ol
6169-06-8

(+)-octan-2-ol

(+)-2-octanoyl retinoate
82838-02-6, 104013-58-3

(+)-2-octanoyl retinoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;96%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

retinoyl chloride
53839-60-4

retinoyl chloride

4-amino-phenol
123-30-8

4-amino-phenol

(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino]-4-hydroxyphenylamide

(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino]-4-hydroxyphenylamide

Conditions
ConditionsYield
With thionyl chloride; triethylamine In N,N-dimethyl-formamide96%
ethanol
64-17-5

ethanol

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

ethyl (all-E)-retinoate
3899-20-5

ethyl (all-E)-retinoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;95%
(i) N,N'-carbonyl-di-imidazole, (ii) /BRN= 1718733/, NaOEt; Multistep reaction;
1,1'-Carbonyl-di-(1,2,4-triazole)
41864-22-6

1,1'-Carbonyl-di-(1,2,4-triazole)

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

1-(all-trans-Retinoyl)-1,2,4-triazol

1-(all-trans-Retinoyl)-1,2,4-triazol

Conditions
ConditionsYield
In acetonitrile for 1h; Heating;95%
In N,N-dimethyl-formamide 1.) RT; 15 min, 2.) 40 deg C, 4 h;87%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(+)-α-phenethyl alcohol
1517-69-7

(+)-α-phenethyl alcohol

(+)-α-phenethylretinoate
82838-01-5, 82863-17-0

(+)-α-phenethylretinoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;95%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(-)-α-phenethylretinoate
82838-01-5, 82863-17-0

(-)-α-phenethylretinoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;95%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

all-trans-retinoic acid-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylester
73880-09-8

all-trans-retinoic acid-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylester

Conditions
ConditionsYield
With pyridine; silver(l) oxide for 1.5h;95%
chloromethyl isobutyrate
61644-18-6

chloromethyl isobutyrate

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid isobutyryloxymethyl ester

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid isobutyryloxymethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 3h; Alkylation;94%
1,3-diethyl 2-diazopropanedioate
5256-74-6

1,3-diethyl 2-diazopropanedioate

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

diethyl 2-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl)oxy)malonate

diethyl 2-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl)oxy)malonate

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;93%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

5-[(fluoromethyl)(4-nitrophenyl)-λ4-sulfanylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

5-[(fluoromethyl)(4-nitrophenyl)-λ4-sulfanylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

(2E,4E,6E,8E)-fluoromethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

(2E,4E,6E,8E)-fluoromethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions
ConditionsYield
With tert-butylimino-tri(pyrrolidino)phosphorane In dichloromethane at 30℃; for 0.166667h; Schlenk technique;93%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

(2-bromoethyl)(hexyl)(2-hydroxyethyl)phosphate
1609100-50-6

(2-bromoethyl)(hexyl)(2-hydroxyethyl)phosphate

2-((2-bromoethoxy)(hexyloxy)phosphoryl)ethoxyretinoate
1609100-56-2

2-((2-bromoethoxy)(hexyloxy)phosphoryl)ethoxyretinoate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine; chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate In dichloromethane for 24h; Inert atmosphere; Reflux;92%
With dmap; N-ethyl-N,N-diisopropylamine; chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate In dichloromethane for 24h; Reflux; Inert atmosphere;92%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

propargyl bromide
106-96-7

propargyl bromide

(2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
58508-30-8

(2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 20℃; for 1h;92%
With caesium carbonate In tetrahydrofuran at 20℃;89%
1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

ferrocenylmethylretinoate

ferrocenylmethylretinoate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;92%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-formylphenyl(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
80850-73-3

4-formylphenyl(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;91%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;91%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

ethylenediamine
107-15-3

ethylenediamine

C22H34N2O
1333107-97-3

C22H34N2O

Conditions
ConditionsYield
Stage #1: all-trans-retinoic-acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 20h;
Stage #2: ethylenediamine In dimethyl sulfoxide at 20℃; for 24h;
91%
Stage #1: all-trans-retinoic-acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice;
Stage #2: ethylenediamine In dichloromethane at 20℃;
63%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

retinoyl fluoride
83802-77-1

retinoyl fluoride

Conditions
ConditionsYield
With (2-chloro-1,2,2-trifluoro-ethyl)-diethyl-amine In tetrahydrofuran for 0.25h; Heating;90%
With perfluoropropylene; diethylamine
With diethylamino-sulfur trifluoride In diethyl ether 1.) -70 deg C, 60 min, 2.) r.t., 2 h;9.1 g
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-(all-trans-retinoyl)-L-phenylalanine methyl ester
110683-03-9

N-(all-trans-retinoyl)-L-phenylalanine methyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Ambient temperature;90%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

EDAC [ethyl-3-(3-dimethylamino)propyl carbodiimide]

EDAC [ethyl-3-(3-dimethylamino)propyl carbodiimide]

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Retinoic Acid N-Hydroxysuccinimide Ester

Retinoic Acid N-Hydroxysuccinimide Ester

Conditions
ConditionsYield
With sodium chloride; argon In ethyl acetate; N,N-dimethyl-formamide90%
With sodium chloride In ethyl acetate; N,N-dimethyl-formamide90%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

N-(all-trans-Retinoyloxy)-succinimide
65646-64-2

N-(all-trans-Retinoyloxy)-succinimide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Darkness;90%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 0.208333h;73%
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 72h;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃; for 3h;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

(2E,4E,6E,8E)-2-cyanoethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
1225383-34-5

(2E,4E,6E,8E)-2-cyanoethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;90%
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Propargylamine
2450-71-7

Propargylamine

(2E,4E,6E,8E)-N-(propargyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

(2E,4E,6E,8E)-N-(propargyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;90%
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