(2Z,4E,6E,8E)-3,7-dimethyl-9-[2-(2H3)methyl-6,6-dimethyl(3,3-2H2)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid

• ChemBase ID: 177449
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1CCC(=C(C1(C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C
• Canonical SMILES: C/C(=C\C=C\C(=C/C(=O)O)\C)/C=C/C1=C(C)CCCC1(C)C
• 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-
• InChIKey: SHGAZHPCJJPHSC-XFYACQKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E,6E,8E)-3,7-dimethyl-9-[2-(^2H₃)methyl-6,6-dimethyl(3,3-^2H₂)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2Z,4E,6E,8E)-3,7-dimethyl-9-[2-(^2H₃)methyl-6,6-dimethyl(3,3-^2H₂)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid
• Synonyms: 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2Z,4E,6E,8E-nonatetranenoic Acid-d5; Isotretinoin-d5; 13-cis-Vitamin A Acid-d5; Accutane-d5; Isotrex-d5; IsotrexGel-d5; Neovitamin A Acid-d5; Ro 4-3780-d5; Roaccutan-d5; Roaccutane-d5; 13-cis-Retinoic Acid-d5

Database IDs

• PubChem SID: 164233359
• PubChem CID: 46782872

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.392896
• LogD (pH = 7.4): 2.6406298
• Log P: 5.0143676
• Molar Refractivity: 97.7908 cm^3
• Polarizability: 36.17498 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R250002

Used as a treatment for severe acne. Presently being studied in conjuction with the treatment of photoaged skin.

REFERENCES

• Lerche, C., et al.: Exp. Dermatol., 17, 972 (2008)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Gan, J., et al.: Chem. Res. Toxicol., 22, 690 (2008)
• Macejova, D., et al.: Toxicol. Lett., 184, 114 (2008)
• Chen, P., et al.: Toxicol. App. Pharmacol.,