3,4-Didehydroretinoic acid
Basic information
- CAS
4159-20-0- Standard SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CC=C1- InChIKey
SYESMXTWOAQFET-YCNIQYBTSA-N- Molecular formula
- C20H26O2
- Average molar mass
- 298.4 g/mol
- Monoisotopic mass
- 298.19328007
Overview
All-trans-3,4-didehydroretinoic acid is a retinoid obtained by 3,4-desaturation of beta-ionone ring of all-trans-retinoic acid. It has a role as a human xenobiotic metabolite. It is a vitamin A and a retinoid. It is functionally related to an all-trans-retinoic acid.
Names & identifiers
- Preferred name
- 3,4-Didehydroretinoic acid
- IUPAC
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraenoic acid
- English name
- 3,4-didehydroretinoic acid
- Molecular formula
- C20H26O2
- Molecular weight
- 298.42
Names & synonyms
4159-20-03,4-Didehydroretinoic acidVitamin A2 acidRo 8-7057DTXSID101310910RefChem:910589DTXCID001740742all-trans-3,4-Didehydro Retinoic Acid(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraenoic acidAll-Trans-3,4-Didehydro-Retinoic acidVitamin A2 saeureVitamin A2 saeure [German]
Show more names
Cambendazole Impurity 13,4-DIDEHYDRO-ALL-TRANS-RETINOICACID(all-E)-3,7-DiMethyl-9-(2,6,6-triMethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenoic Acid(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)nona-2,4,6,8-tetraenoic acid
3-Dehydroretinoic AcidRetinoic acid, 3,4-didehydro-didehydroretinoic acidVitamin A Impurity 49orb2695206SCHEMBL2897706all-trans-3,4-DidehydroretinoateCHEBI:133794
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 606
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Physicochemical properties
- Melting point
- 175 · 175-177 °C
- Boiling point
- 468.2 · 468.2±14.0 °C(Predicted)
- Density
- 1.027 · 1.027±0.06 g/cm3(Predicted)
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 4.73 · 4.73±0.33(Predicted)
- color
- Yellow
- Stability
- Light Sensitive, Temperature Sensitive
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesA Retinoic Acid derivative for the treatment of neuroinflammatory conditions.
Additional notes
DefinitionChEBI: A retinoid obtained by 3,4-desaturation of beta-ionone ring of all-trans-retinoic acid
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