Vitamin A2

Base Information

• Chemical Name: Vitamin A2
• CAS No.: 79-80-1
• Molecular Formula: C20H28 O
• Molecular Weight: 284.442
• European Community (EC) Number: 201-226-4
• UNII: 104621892X
• DSSTox Substance ID: DTXSID401018959
• Nikkaji Number: J4.241B
• Wikipedia: Vitamin_A2
• Wikidata: Q24390934
• Metabolomics Workbench ID: 29031
• ChEMBL ID: CHEMBL1797132
• Mol file: 79-80-1.mol

Synonyms:3,4-didehydroretinol;3-dehydroretinol;vitamin A2;vitamin A2, (7-cis)-isomer

Chemical Property of Vitamin A2

Chemical Property:

• Vapor Pressure: 5.01E-09mmHg at 25°C
• Melting Point: 63-650C
• Boiling Point: 425.6°C at 760 mmHg
• Flash Point: 151.4°C
• PSA: 20.23000
• Density: 0.969g/cm³
• LogP: 5.28630
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 284.214015512
• Heavy Atom Count: 21
• Complexity: 534

Purity/Quality:

99%, ^*data from raw suppliers

3-DehydroRetinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC=C1)(C)C)C=CC(=CC=CC(=CCO)C)C
• Isomeric SMILES: CC1=C(C(CC=C1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
• Uses: Naturally occurring retinoid originally discovered in livers of freshwater fish. Constitutes 20-25% of total retinoid content in human epidermis; levels are markedly elevated in patients with hyperproliferative dermatoses such as psoriasis Naturally occurring retinoid originally discovered in livers of freshwater fish. Constitutes 20-25% of total retinoid content in human epidermis; levels are markedly elevated in patients with hyperproliferative dermatoses such as psoriasis.

Technology Process of Vitamin A2

There total 21 articles about Vitamin A2 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: 99.0%

ethyl 3,4-didehydroretinoate (26918-26-3) → vitamin A2 (79-80-1)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1039/b411585f

Reference yield:

1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene (817203-14-8) → vitamin A2 (79-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / AsPh₃ / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 4 h / 70 °C

2: 99 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

With triphenyl-arsane; diisobutylaluminium hydride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; 1: Stille cross-coupling;

DOI:10.1039/b411585f

Reference yield:

ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-(tri-n-butylstannyl)nona-2,4,6,8-tetraenoate → vitamin A2 (79-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / AsPh₃ / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 4 h / 70 °C

2: 99 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

With triphenyl-arsane; diisobutylaluminium hydride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; 1: Stille cross-coupling;

DOI:10.1039/b411585f

upstream raw materials:

3,4-didehydroretinal

(Z)-3-methylpent-2-en-4-ynol

(E)-2-Methyl-4-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-but-2-enal

RETINOL

Downstream raw materials:

3,4-didehydroretinal

9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-[2.2.6-trimethyl-cyclohexadien-(4.6)-(yl)-nonatetraen-(1.3t.5t.7t)

ethyl-[4-(3,7-dimethyl-nona-2,4,6,8-tetraenylidene)-3,5,5-trimethyl-cyclohex-2-enyl]-ether

3-hydroxyretinol

Refernces

• 1、 Barckhausen, Ian R.,Child, Stella A.,Glass, Sarah M.,Goldfarb, Margo H.,Guengerich, F. Peter,Reddish, Michael J.. "Functional interactions of adrenodoxin with several human mitochondrial cytochrome P450 enzymes". . . Retrieved 2020/10/02.
• 2、 Dominguez, Marta,Alvarez, Rosana,Martras, Silvia,Farres, Jaume,Pares, Xavier,De Lera, Angel R.. "Synthesis of ring-oxidized retinoids as substrates of mouse class I alcohol dehydrogenase (ADH1)". . p. 3368 - 3373. Retrieved 2007/10/03.