Retinoic acid chloride

Base Information

• Chemical Name: Retinoic acid chloride
• CAS No.: 53839-60-4
• Molecular Formula: C₂₀H₂₇ClO
• Molecular Weight: 318.887
• UNII: NUK8E8CBQ8
• Nikkaji Number: J1.141.041C
• Mol file: 53839-60-4.mol

Synonyms:retinoic acid chloride;retinoyl chloride;53839-60-4;Vitamin A acid chloride;NUK8E8CBQ8;all-trans-retinoyl chloride;UNII-NUK8E8CBQ8;2,4,6,8-Nonatetraenoyl chloride, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl chloride;OBWAFSRXIGEEKA-YCNIQYBTSA-N

Chemical Property of Retinoic acid chloride

Chemical Property:

• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 318.1750432
• Heavy Atom Count: 22
• Complexity: 569

Purity/Quality:

Retinoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)Cl)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)Cl)/C)/C
• Uses: Retinoyl Chloride is used to synthesize retinyl ascorbate (RA-AsA) which is a co-drug for the purpose of treating damage to skin resulting from UV-induced production of free radicals.

Technology Process of Retinoic acid chloride

There total 12 articles about Retinoic acid chloride 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:

all-trans-retinoic-acid (302-79-4) → retinoyl chloride (53839-60-4)

Guidance literature:

With oxalyl dichloride; In benzene; for 1h; Ambient temperature;

DOI:10.1021/jm00167a034

Reference yield:

all-trans-retinoic-acid (302-79-4) + 4-acetamidothiophenol (1126-81-4) → Retinoic Acid 4-Acetamidophenyl Thioester + retinoyl chloride (53839-60-4)

Guidance literature:

With phosphorus trichloride; pyridine; In tetrahydrofuran; toluene;

Reference yield:

4-(methyltri-O-acetyl) aminophenyl-C-glucuronide + all-trans-retinoic-acid (302-79-4) → retinoyl chloride (53839-60-4)

Guidance literature:

With pyridine; thionyl chloride; In benzene;

upstream raw materials:

all-trans-retinoic-acid

diazomethane

2,3,4,6-tetra-O-acetylglucopyranosyl 1-amine

sulfuric acid

Downstream raw materials:

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

retinoic anhydride

1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-retinamidobenzene

all-trans-methyl retinoate

Refernces

• 1、 -. "COSMETIC COMPOSITION FOR SKIN WHITENING COMPRISING RETINOIDS DERIVATIVE AS ACTIVE INGREDIENT". Paragraph 0058. . Retrieved 2018/05/03.
• 2、 -. "Podophyllotoxin-retinoic acid heterocomplex synthesis method and application of podophyllotoxin-retinoic acid heterocomplex in medicine for preventing and curing tumors". Paragraph 0018. . Retrieved 2017/09/01.