Anhydrovitamin A

Base Information

• Chemical Name: Anhydrovitamin A
• CAS No.: 1224-78-8
• Molecular Formula: C20H28
• Molecular Weight: 268.442
• UNII: 235BBF3K97
• DSSTox Substance ID: DTXSID101123105
• Nikkaji Number: J1.649.583B
• Wikidata: Q27253719
• Metabolomics Workbench ID: 147463
• Mol file: 1224-78-8.mol

Synonyms:anhydroretinol;anhydrovitamin A;trans-anhydrovitamin A

Chemical Property of Anhydrovitamin A

Chemical Property:

• Vapor Pressure: 1.37E-05mmHg at 25°C
• Melting Point: 65-70°C
• Boiling Point: 378.4°Cat760mmHg
• Flash Point: 171.7°C
• PSA: 0.00000
• Density: 0.902g/cm³
• LogP: 6.31390
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 268.219100893
• Heavy Atom Count: 20
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

all-trans-AnhydroRetinol(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A reproductive hazard.
• Hazard Codes: A reproductive hazard.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C1=CC=C(C)C=CC=C(C)C=C)(C)C
• Isomeric SMILES: CC\1=CCCC(/C1=C\C=C(/C)\C=C\C=C(/C)\C=C)(C)C
• Uses: A metabolite of vitamin A (Retinol) (R252000).

Technology Process of Anhydrovitamin A

There total 18 articles about Anhydrovitamin A 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: 67.0%

RETINOL (68-26-8) → Anhydro-retinol (1224-78-8)

Guidance literature:

RETINOL; With trifluorormethanesulfonic acid; In chloroform;

With methanol; In chloroform; at 20 ℃; for 0.0166667h; Further stages.;

DOI:10.1039/b709535j

Reference yield:

Retinol acetate (127-47-9,64536-04-5) → anhydroretinol (1224-78-8,7245-10-5,20603-89-8,70268-03-0,70268-04-1,70268-05-2,144407-18-1) + retinyl methyl ether (32450-56-9) + 9-cis-Vitamin-A-acetat (29584-22-3,64536-04-5) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5,64536-04-5)

Guidance literature:

In methanol; for 0.166667h; Irradiation;

DOI:10.1016/S0040-4039(00)97417-3

Reference yield:

RETINOL (68-26-8) → anhydroretinol (1224-78-8,7245-10-5,20603-89-8,70268-03-0,70268-04-1,70268-05-2,144407-18-1) + vitamin A2 (79-80-1) + all-(E)-Retroretinol (16729-22-9) + 12-(Z)-Retroretinol

Guidance literature:

With dihydrogen peroxide; iron(III) tetraphenylporphyrin; In methanol; dichloromethane; at 30 ℃; for 24h; Yield given. Further byproducts given. Yields of byproduct given;

upstream raw materials:

Retinol acetate

RETINOL

2-((1E,3E,5E,7Z)-3,7-Dimethyl-9-prop-2-ynyloxy-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

2-((1E,3E,5E,7E)-3,7-Dimethyl-9-prop-2-ynyloxy-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

Refernces

• 1、 Kildahl-Andersen, Geir,Naess, Stine Nalum,Aslaksen, Petter B.,Anthonsen, Thorleif,Liaaen-Jensen, Synnove. "Studies on the mechanism of the Carr-Price blue colour reaction". . p. 3027 - 3033. Retrieved 2007.
• 2、 Alvarez, Rosana,Iglesias, Beatriz,Lopez, Susana,De Lera, Angel R.. "Stereocontrolled synthesis of all-(E)- and (8Z)-anhydroretinol". . p. 5659 - 5662. Retrieved 2007/10/03.
• 3、 Waldmann, Doris,Koenig, Thorsten,Schreier, Peter. "Iron(III)Porphinate/H2O2-Mediated Conversion of All-(E)-Retinol". . p. 589 - 594. Retrieved 2007/10/02.