3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl propanoate

• ChemBase ID: 155867
• Molecular Formular: C23H34O2
• Molecular Mass: 342.51486
• Monoisotopic Mass: 342.25588033
• SMILES: CCC(=O)OC/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(CCCC1(C)C)C
• Canonical SMILES: CCC(=O)OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
• InChI: InChI=1S/C23H34O2/c1-7-22(24)25-17-15-19(3)11-8-10-18(2)13-14-21-20(4)12-9-16-23(21,5)6/h8,10-11,13-15H,7,9,12,16-17H2,1-6H3
• InChIKey: SFRPDSKECHTFQA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl propanoate; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl propanoate
• IUPAC Traditional name: 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl propanoate; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl propanoate
• Synonyms: Vitamin A propionate; Retinyl propionate; Retinol propionate; 15-Retinol Propanoate; all-trans-Retinol Propionate; Retinyl Propionate

Database IDs

• CAS Number: 7069-42-3
• EC Number: 230-363-2
• MDL Number: MFCD00129785
• Beilstein Number: 2475675
• PubChem SID: 162250005; 24888741
• PubChem CID: 6394572

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.8357544
• LogD (pH = 7.4): 5.8357544
• Log P: 5.8357544
• Molar Refractivity: 111.7018 cm^3
• Polarizability: 41.977844 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 128 °C; 262.4 °F

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 63-38
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of isomers, HPLC)
• Impurities: ~5% cis-isomers
• Contains: BHT as stabilizer
• Empirical Formula (Hill Notation): C23H34O2

DETAILS

Sigma Aldrich - 87809

Unit Definition
1 international unit according to PH EUR II, 217 (1983)
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinyl propionate is used in various formulations to control wrinkles.

Toronto Research Chemicals - R275550

Retinyl Propionate is a Vitamin A ester derivative. Retinyl Propionate is a hypermitotic agent that is used in cosmetic formulations.

REFERENCES

• Ridge, B.D. et al.: Br. J. Dermatol., 118, 167 (1988)
• Oblong, J.E. et al.: Cosm. Sci. Technol., Ser., 27, 441 (1988)
• Weisse, S. et al.: J. Drug Del. Sci. Technol., 14, 77 (1988)