(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-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: 169482
• Molecular Formular: C42H58O6
• Molecular Mass: 658.90632
• Monoisotopic Mass: 658.42333958
• SMILES: C1[C@@H](C[C@@]2([C@@](C1(C)C)(CC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C=C1C(C[C@@H](C[C@]1(O)C)OC(=O)C)(C)C)\C)\C)/C)/C)O2)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/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1
• InChIKey: SJWWTRQNNRNTPU-ABBNZJFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-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: all-trans-fucoxanthin
• Synonyms: (3S,3'S,5R,5'R,6S,6'R)-6',7'-Didehydro-5,6-epoxy-4',5',6,7-tetrahydro-3,3',5'-trihydroxy-β,β-caroten-8(5H)-one; all-trans-Fucoxanthin; FucoxanthinDISCONTINUED

Database IDs

• CAS Number: 3351-86-8
• PubChem SID: 162263614
• 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

Physical Property

• Solubility: Ethanol
• Apperance: Crystalline Solid
• Melting Point: 160°C

DETAILS

Toronto Research Chemicals - F810500

A carotenoid pigment found in fresh brown algae.

REFERENCES

• Olaizola, M., et al.: J. Phycol., 30, 606 (1994)
• Falkowski, P., et al.: Science, 290, 291(1994)
• Kashino, Y., et al.: Biochemistry, 41, 8004 (1994)
• Strzepek, R., et al.: Nature, 431, 689 (1994)
• Wehner, A., et al.: J. Biol. Chem., 279, 2682 (1994)