(1S,3R)-3-hydroxy-4-{18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

• ChemBase ID: 154591
• Molecular Formular: C42H58O6
• Molecular Mass: 658.90632
• Monoisotopic Mass: 658.42333958
• SMILES: C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)C[C@]12[C@](O1)(C[C@H](CC2(C)C)O)C)/C=C/C=C(\C)/C=C=C1[C@](C[C@H](CC1(C)C)OC(=O)C)(C)O
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C
• InChI: InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/t23?,34-,35-,40+,41+,42-/m0/s1
• InChIKey: SJWWTRQNNRNTPU-BUCUEIECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R)-3-hydroxy-4-{18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate
• IUPAC Traditional name: (1S,3R)-3-hydroxy-4-{18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate
• Synonyms: all-trans-Fucoxanthin; Fucoxanthin

Database IDs

• CAS Number: 3351-86-8
• MDL Number: MFCD01745140
• PubChem SID: 162248729
• PubChem CID: 5281239

CALCULATED PROPERTIES

• Acid pKa: 14.033714
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.8277016
• LogD (pH = 7.4): 6.8277016
• Log P: 6.8277016
• Molar Refractivity: 202.7592 cm^3
• Polarizability: 76.20058 Å^3
• Polar Surface Area: 96.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C42H58O6

DETAILS

Sigma Aldrich - F6932

Biochem/physiol Actions
Xanthophyll carotenoid pigment extracted from algae. Exhibits anticancer, antioxidant, anti-obesity and anti-inflammatory properties.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F6932.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.