Retinoic acid

C₂₀H₂₈O₂CAS 302-79-4300.44 g/mol

Open in Covalent MOL file

Alkene Carboxylic acid

Properties

Molecular formula: C₂₀H₂₈O₂
Molar mass: 300.44 g/mol
Exact mass: 300.2089 Da
Melting point: 180–182 °C
Water solubility: < 1 g/L (25 °C)
logP: 5.60Crippen estimate
Polar surface area: 37.3 Å²
H-bond donors / acceptors: 1 / 1
Rotatable bonds: 5
Double bonds: E, E, E, EE/Z, in SMILES order

Hazards

Danger

H302 Harmful if swallowed29.8% of notifiers
H315 Causes skin irritation73.4% of notifiers
H319 Causes serious eye irritation16.5% of notifiers
H335 May cause respiratory irritation14.9% of notifiers
H360 May damage fertility or the unborn child72.9% of notifiers
H400 Very toxic to aquatic life59% of notifiers
H410 Very toxic to aquatic life with long lasting effects58% of notifiers
H411 Toxic to aquatic life with long lasting effects16% of notifiers

Aggregated from 188 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501

Identifiers

CAS number

302-79-4

SMILES

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1

InChIKey

SHGAZHPCJJPHSC-YCNIQYBTSA-N

InChI

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

34 names · show all

NSC 122758
Retacnyl
Retinoic acid, all-trans-
Vitamin A acid
Tretinoin
trans-Retinoic acid
2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
All-trans-Vitamin A acid
Vitamin A acid, all-trans-
Vitamin A1 acid, all-trans-
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
β-Retinoic acid
(All-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
All-trans-Tretinoin
All-(E)-Retinoic acid
Tretin M
All-trans-β-Retinoic acid
Ro 1-5488
Retin A
AGN 100335
Aberel
All-trans-Retinoic acid
Vesanoid
ATRA
Renova
Atragen
Vesnaroid
Epi-aberel
Cordes vas
Dermairol
Aknoten
Airol
NSC 122578
Eudyna

Work with Retinoic acid

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Isotretinoin4759-48-2Stereoisomer 9-cis-Retinoic acid5300-03-8Stereoisomer

Similar compounds

Beta-carotene7235-40-773 % similar Retinal116-31-469 % similar Vitamin A11103-57-466 % similar Retinol68-26-866 % similar Retinyl retinoate15498-86-965 % similar Hydroxypinacolone retinoate893412-73-263 % similar Retinyl acetate127-47-962 % similar Fenretinide65646-68-662 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Same formula

17Beta-Hydroxy-17-methylandrosta-4,9(11)-dien-3-one1039-17-4 5,8,11-Eicosatriynoic acid13488-22-7 Dehydroabietic acid1740-19-8 13-Ethyl-3-methoxygona-2,5(10)-dien-17-one2322-77-2 Methandrostenolone72-63-9

Elsewhere

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