(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

• ChemBase ID: 155625
• Molecular Formular: C20H28O4
• Molecular Mass: 332.43392
• Monoisotopic Mass: 332.19875938
• SMILES: CC(C)c1cc2c(c(c1O)O)[C@]1(CCCC([C@@H]1CC2)(C)C)C(=O)O
• Canonical SMILES: OC(=O)[C@@]12CCCC([C@@H]2CCc2c1c(O)c(c(c2)C(C)C)O)(C)C
• InChI: InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
• InChIKey: QRYRORQUOLYVBU-VBKZILBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
• IUPAC Traditional name: salvin
• Synonyms: Carnosic acid from Rosmarinus officinalis; (4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydro-2H-phenanthrene-4a-carboxylic acid; Salvin; Carnosic acid

Database IDs

• CAS Number: 3650-09-7
• MDL Number: MFCD02259459
• Beilstein Number: 2707918
• PubChem SID: 162249763
• PubChem CID: 65126

CALCULATED PROPERTIES

• Acid pKa: 4.2929454
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.9104488
• LogD (pH = 7.4): 2.1704886
• Log P: 5.141634
• Molar Refractivity: 93.4058 cm^3
• Polarizability: 36.217587 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥91%; ≥97.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H28O4

DETAILS

Sigma Aldrich - C0609

Frequently Asked Questions
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Application
Phenolic compound that is naturally occurring with antioxidant properties. Inhibits lipid peroxidation which is caused by NADH or NADPH oxidation.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C0609.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.