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Tretinoin
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Name

Tretinoin

 EINECS 206-129-0
CAS No. 302-79-4 Density 1.011 g/cm3
PSA 37.30000 LogP 5.60260
Solubility insoluble in water Melting Point 179-184 °C
Formula C20H28O2 Boiling Point 462.8 °C at 760 mmHg
Molecular Weight 300.441 Flash Point 350.6 °C
Transport Information N/A Appearance yellow-orange powder
Safety 53-26-36/37/39-45-36/37 Risk Codes 22-63-38-20/21/22
Molecular Structure Molecular Structure of 302-79-4 (Tretinoin) Hazard Symbols ToxicT,HarmfulXn
Synonyms

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoate;all-trans-beta-Retinoic acid;Vitamin A acid;Tretinoine (French) (EINECS);Retin A;trans-Retinoic acid;all-trans-Vitamin A1 acid;Acide retinoique (French) (DSL);2,4, 6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-, (2E, 4E, 6E, 8E)-;all-trans-Retinoate;AGN 100335;Vitamin A acid sodium salt;Vitamin A1 acid, all-trans-;ATRA;Retin-A;Vesnaroid;Tretin M;all-(E)-Retinoic acid;Retinoic acid, sodium salt;beta-Retinoic acid;Cordes Vas;Aberel;Tretinoin, all-trans-;Retionic acid;Dermairol;Eudyna;Aknefug;Retinoate;all-trans-Retinoic acid;Retacnyl;Tretinoin (all-trans retinoic acid );Tretinoin USP26;

Article Data 98

Tretinoin Synthetic route

3899-20-5

ethyl (all-E)-retinoate

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%
68-26-8

RETINOL

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
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

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

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%
54168-84-2

trans-β-formyl crotonic acid

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

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%
54168-84-2

trans-β-formyl crotonic acid

53282-28-3

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

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%
116-31-4

all-trans-Retinal

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;
3899-20-5, 51249-34-4, 59699-82-0, 85354-08-1, 86708-67-0, 86708-68-1, 86708-69-2, 86708-70-5

ethyl retinoate

A

4759-48-2

13-cis-retinoic acid

B

302-79-4

all-trans-retinoic-acid

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%
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

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%
20013-34-7

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

302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With pyridine In dichloromethane67%
38987-91-6

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

19041-16-8

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

Tretinoin Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Tretinoin Specification

The Tretinoin, with the CAS registry number 302-79-4,is also known as 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; all-trans-Retinoic acid; Vitamin A acid. It belongs to the product categories of Intermediates & Fine Chemicals;Retinoids;Intracellular receptor;API.Its EINECS number is 206-129-0. This chemical's molecular formula is C20H28O2 and molecular weight is 300.44. What's more,Its systematic name is Tretinoin.It is a yellow-orange powder which has been used to treat acne and other skin problems, and can be used for the unusual type of acne, psoriasis ichthyosis and abnormal.

Physical properties about Tretinoin are:
(1)ACD/LogP:  6.83; (2)# of Rule of 5 Violations:  1; (3)ACD/LogD (pH 5.5):  5.99; (4)ACD/LogD (pH 7.4):  4.19; (5)ACD/BCF (pH 5.5):  13226.03; (6)ACD/BCF (pH 7.4):  210.25; (7)ACD/KOC (pH 5.5):  17912.95; (8)ACD/KOC (pH 7.4):  284.76; (9)#H bond acceptors:  2; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  5; (12)Index of Refraction:  1.556; (13)Molar Refractivity:  95.527 cm3; (14)Molar Volume:  297.151 cm3; (15)Surface Tension:  39.1399993896484 dyne/cm; (16)Density:  1.011 g/cm3; (17)Flash Point:  350.596 °C; (18)Enthalpy of Vaporization:  79.324 kJ/mol; (19)Boiling Point:  462.801 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.3. Structure Descriptors of Tretinoin

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C;
(2)Std. InChI:InChI=1S/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)/b9-6+,12-11+,15-8+,16-14+;
(3)Std. InChIKey:SHGAZHPCJJPHSC-YCNIQYBTSA-N.

Safety Information of Tretinoin:
The Tretinoin is harmful by inhalation, in contact with skin and if swallowed and rritating to skin. It is possible risk of harm to the unborn child. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .When you use it wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. This chemical is danger to the environment Avoid exposure - obtain special instructions before use.

Toxicity of Tretinoin is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 208mg/kg (208mg/kg)   Drugs in Japan Vol. -, Pg. 886, 1995.
mouse LD50 intravenous 92mg/kg (92mg/kg)   United States Patent Document. Vol. #3878202,
mouse LD50 oral 1100mg/kg (1100mg/kg)   American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
mouse LD50 subcutaneous 253mg/kg (253mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat LD50 intraperitoneal 96mg/kg (96mg/kg) SPINAL CORD: OTHER DEGENERATIVE CHANGES

BEHAVIORAL: ATAXIA

BLOOD: NORMOCYTIC ANEMIA		 Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat LD50 intravenous 75mg/kg (75mg/kg)   Drugs in Japan Vol. -, Pg. 886, 1995.
rat LD50 oral 2gm/kg (2000mg/kg)   American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
rat LD50 subcutaneous 53mg/kg (53mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.

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