Tretinoin

Base Information

• Chemical Name: Tretinoin
• CAS No.: 302-79-4
• Deprecated CAS: 56573-65-0,7005-78-9,187175-63-9,7005-78-9
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• Hs Code.: 29362100
• European Community (EC) Number: 206-129-0
• NSC Number: 759631,122758
• UNII: 5688UTC01R
• DSSTox Substance ID: DTXSID7021239
• Nikkaji Number: J1.313.469C,J2.378.058E,J494.243D,J528.606I,J623.910B,J690.379G,J1.518K,J646.157C,J646.158A,J970.183D
• Wikipedia: Tretinoin
• Wikidata: Q29417
• NCI Thesaurus Code: C900,C2398
• RXCUI: 10753
• Pharos Ligand ID: AAM7T1JPHW13
• Metabolomics Workbench ID: 29042
• ChEMBL ID: CHEMBL38
• Mol file: 302-79-4.mol

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;

Chemical Property of Tretinoin

Chemical Property:

• Appearance/Colour: yellow-orange powder
• Vapor Pressure: 7.55E-10mmHg at 25°C
• Melting Point: 179-184 °C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 462.8 °C at 760 mmHg
• PKA: 4.73±0.33(Predicted)
• Flash Point: 350.6 °C
• PSA: 37.30000
• Density: 1.011 g/cm³
• LogP: 5.60260
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent).
• Water Solubility.: insoluble
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 567

Purity/Quality:

99% min ^*data from raw suppliers

Retinoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn,N
• Statements: 22-63-38-20/21/22-51/53
• Safety Statements: 53-26-36/37/39-45-36/37-61-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: Treatment of striae distensae with fractional radiofrequency and topical tretinoin: An intra-individual study with blinded outcome assessment
• Recent NIPH Clinical Trials: Clinical study on the safety and usefulness of Cyclodextrin inclusion welding Tretinoin for wrinkles and pigmentation of the skin
• General Description: Tretinoin, also known as all-trans-retinoic acid (ATRA), is a biologically active metabolite of vitamin A that plays a vital role in regulating cell proliferation, differentiation, and morphogenesis. It functions by binding to retinoic acid receptors (RARs), influencing processes such as embryonic development, immune function, and skin health. Tretinoin is widely used in dermatology for its efficacy in treating acne and photoaging, as well as in oncology for its ability to induce differentiation in certain cancer cells, such as acute promyelocytic leukemia (APL). Its derivatives and analogs, including synthetic retinoids, are explored for improved selectivity and reduced toxicity in therapeutic applications.

Technology Process of Tretinoin

There total 165 articles about Tretinoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3) → 9-cis-retinoic 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)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1055/s-2001-14908

Reference yield: 98.0%

ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3) + potassium hydroxide → 9-cis-retinoic 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)

Guidance literature:

With water; In ethanol; at 50 ℃;

DOI:10.1039/b813760a

Reference yield: 83.0%

(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester (24519-09-3) → 9-cis-retinoic 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)

Guidance literature:

With potassium hydroxide; In ethanol; at 70 ℃; for 3h;

DOI:10.1021/jo952189g

upstream raw materials:

ethyl 3-methylbut-2-enoate

(2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal

9,13-di-cis-retinoic acid

diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate

Downstream raw materials:

[7t,9c,11t,13t]retinoic acid methyl ester

retinoyl chloride

ethyl (all-E)-retinoate

cholesteryl retinoate

Refernces

Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids

10.1016/j.tetlet.2009.06.032

The study focuses on the cross metathesis (CM) reactions of β-carotene with electron-deficient dienes, specifically using the Hoveyda second generation catalyst, to synthesize retinoids, which are compounds related to vitamin A and play a crucial role in various biological processes such as vision, reproduction, cell differentiation, and growth. The primary chemicals used in the study include β-carotene, ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate, and the Hoveyda II catalyst. The purpose of these chemicals is to undergo CM reactions, which are a type of olefin metathesis reaction that forms new carbon-carbon bonds under mild conditions, to produce retinoids like ethyl all-trans-retinoate. The study explores the regioselectivity and diastereoselectivity of these reactions, aiming to develop an effective and fast method for the preparation of retinoids for biological and structural studies.

Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide

10.1016/S0014-827X(01)01074-6

The research aimed to synthesize and test the biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide (4-HPR), a synthetic derivative of retinoic acid, on various tumor cell lines. The purpose was to investigate the potential antiproliferative effects and reduced toxicity of these conjugates compared to the parent compound, 4-HPR. The study focused on glucosyl, galactosyl, and mannosyl conjugates, which were synthesized through a five-step process involving the use of peracetylated monosaccharides, bismuth bromide as a catalyst, p-nitrophenol, Pearlman’s catalyst for nitro group reduction, and EDC/DMAP for coupling with RA. The synthesized compounds were then tested for their antiproliferative potential in vitro using four human cancer cell lines and their toxicity on normal cells. The results showed that all three conjugates were active on promyelocytic leukemia cell lines HL60 but were less potent than 4-HPR. Notably, the mannosyl analog (5c) demonstrated significantly lower toxicity than 4-HPR, with a selectivity index close to 15 on HL60 cells, indicating its potential as a less toxic and effective antiproliferative agent.

Design, synthesis and evaluation of retinoids with novel bulky hydrophobic partial structures

10.1016/j.bmc.2013.04.053

Retinoic acid, specifically all-trans-retinoic acid (ATRA), is an active metabolite of vitamin A. It plays a crucial role in regulating various critical biological functions, including cell proliferation, morphogenesis, and the differentiation of embryonic stem cells and committed cells such as blood, dermal, immunological, and neuronal cells. ATRA achieves these functions by activating retinoic acid receptors (RARs). The study highlights that ATRA and related compounds, collectively known as retinoids, have been extensively investigated for their chemistry and biology. The research aims to develop new retinoids that selectively bind to RARs without activating retinoic acid X receptors (RXRs), which is important for therapeutic applications. The study evaluates the agonistic activities of newly synthesized retinoids towards RARs and RXRs, with the goal of finding compounds that are more selective and effective than existing retinoids like ATRA and tamibarotene (Am80).