(2E,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: 177450
• 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-YCNIQYBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,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: (2E,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: (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid-d5; Vitamin A Acid-d5; ATRA-d5; Aberel-d5; Avita-d5; Retin-A-d5; Retinova-d5; Tretinoin-d5; all-trans-Retinoic Acid-d5

Database IDs

• PubChem SID: 164233360
• PubChem CID: 12358676

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: Dimethyl Sulfoxide (25mg/ml); Ethanol (25 mg/ml)
• Apperance: Yellow solid
• Melting Point: 168-173°C

Safety Information

• Storage Condition: Amber Vial, -86?C Freezer, Under Inert Atmosphere
• Storage Warning: Store Dry in Freezer at -20°C for up to 1 year.

DETAILS

Toronto Research Chemicals - R250202

An isotopically Labelled analog of retinoic acid. Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation.A representative lot contains 11% d4, no d0 or d1 pres

REFERENCES

• Kamm, J.J., et al.: J. Am. Acad. Dermatol., 6, 652 (1982)
• Warrel, R.P., et al.: Leukemia, 8, 929 (1982)
• Sasai, Y., et al.: J. Neurol., 249, 41 (1982)