(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

• ChemBase ID: 128135
• Molecular Formular: C40H56O2
• Molecular Mass: 568.87144
• Monoisotopic Mass: 568.42803103
• SMILES: CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C)/C)/C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C)\C
• InChI: InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/t35-,36+,37-/m0/s1
• InChIKey: KBPHJBAIARWVSC-QOEXFKEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol; (1R)-4-{18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol; (1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol
• IUPAC Traditional name: (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol; (1R)-4-{18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol; carotenoid
• Synonyms: (3R,3'R,6'R)-β,ε-Carotene-3,3'-diol; (3R,3'R,6'R)-Lutein; (all-E)-Lutein; 6'-Hydro-4',5'-dehydro-β-carotene-3,3'-diol; Bo-Xan; E 161; E 161b; FloraGLO; FloraGLO Lutein; Lutein; Lutein A; OS 24; Oro Glo 7; Vegetable Lutein; all-trans-(+)-Xanthophyll; Xanthophyll; Luteine; trans-lutein; 4-​[18-​(4-​Hydroxy-​2,6,6-​trimethyl-​1-​cyclohexenyl)-​3,7,12,16-​tetramethyloctadeca-​1,3,5,7,9,11,13,15,17-​nonaenyl]-​3,5,5-​trimethyl-​cyclohex-​2-​en-​1-​ol; Lutein; Lutein

Database IDs

• CAS Number: 127-40-2
• PubChem SID: 162222449
• PubChem CID: 5281243
• CHEBI ID: 28838
• CHEMBL: 173929
• Chemspider ID: 4444655
• Unique Ingredient Identifier: X72A60C9MT
• Wikipedia Title: Lutein

CALCULATED PROPERTIES

• Acid pKa: 18.217272
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 8.550209
• LogD (pH = 7.4): 8.550209
• Log P: 8.550209
• Molar Refractivity: 195.0634 cm^3
• Polarizability: 71.71594 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Soluble in fats
• Apperance: Coppery powder; Red-orange crystalline solid
• Melting Point: 190 °C

Safety Information

• Safety Statements: R

Product Information

• Purity: 96.0; 97%

DETAILS

Toronto Research Chemicals - X742000

One of the most widespread carotenoid alcohols in nature. Originally isolated from egg yolk, also isolated by chromatography from nettles, algae, and petals of many yellow flowers.

REFERENCES

• van het Hof, K., et al.: J. Nutr., 130, 503 (2000)
• Cooper, D., et al.: J. Nutr., 134, 221S (2000)
• Faulks, R., et al.: Biochim. Biophys. Acta, 1740, 95 (2000)
• Rao, A., et al.: Pharmacol. Res., 55, 207 (2000)
• Tuberoso, C., et al.: Food Chem., 103, 149 (