4-[18-(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: 23
• Molecular Formular: C40H56O2
• Molecular Mass: 568.87144
• Monoisotopic Mass: 568.42803103
• SMILES: OC1CC(C(C(=C1)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(CC(O)CC1(C)C)C)\C)\C)/C)/C)(C)C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CC(CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1C(=CC(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/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
• InChIKey: KBPHJBAIARWVSC-DKLMTRRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[18-(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; 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(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: 4-[18-(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; xanthophyll
• Brand Name: Bo-Xan
• Synonyms: (3R,3'R)-Beta,Beta-Carotene-3,3'-Diol, Lutein; (3R,3'R,6'R)-Lutein; (3R,3'R,6S)-4,5-Didehydro-5,6-Dihydro-Beta,Beta-Carotene-3,3'-Diol; 4,5-Didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diol; All-trans-(+)-Xanthophyll; All-trans-Lutein; all-trans-Xanthophyll; beta,epsilon-Carotene-3,3'-diol; Lutein ester; Phylloxanthin; trans-Lutein; Carotenoid; Lutein; Luteine; Vegetable lutein; Vegetable luteol; Xanthophyll

Database IDs

• CAS Number: 127-40-2
• EC Number: 204-840-0
• PubChem SID: 46508835; 160963486
• PubChem CID: 5368396

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 8.29
• LOG S: -5.89
• Solubility (Water): 7.32e-04 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 7.9

Safety Information

• Storage Condition: Room Temperature (15-30°C)

DETAILS

MP Biomedicals - 02103292

Xanthophyll is primarily crystalline lutein obtained from marigold oleoresin and is a 20% suspension in corn oil base.

DrugBank - DB00137

• Drug Groups: approved; nutraceutical
• Description: Xanthophylls are yellow pigments from the carotenoid group that are widespread in nature. They are present in egg yolk, algae, and petals of yellow flowers, among other sources. The xanthophylls include lutein, zeaxanthin, neoxanthin, violaxanthin, and α- and β-cryptoxanthin, of which lutein is the primary ingested one.
• Indication: Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.
• Pharmacology: Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).
• Affected Organisms: Humans and other mammals
• References: Namitha KK, Negi PS: Chemistry and biotechnology of carotenoids. Crit Rev Food Sci Nutr. 2010 Sep;50(8):728-60. [Pubmed] ; Ma L, Lin XM: Effects of lutein and zeaxanthin on aspects of eye health. J Sci Food Agric. 2010 Jan 15;90(1):2-12. [Pubmed]
• External Links: Wikipedia; PDRhealth

REFERENCES

• Namitha KK, Negi PS: Chemistry and biotechnology of carotenoids. Crit Rev Food Sci Nutr. 2010 Sep;50(8):728-60. Pubmed
• Ma L, Lin XM: Effects of lutein and zeaxanthin on aspects of eye health. J Sci Food Agric. 2010 Jan 15;90(1):2-12. Pubmed