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127-40-2 molecular structure
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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

ChemBase ID: 23
Molecular Formular: C40H56O2
Molecular Mass: 568.87144
Monoisotopic Mass: 568.42803103
SMILES and InChIs

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

Cite this record

CBID:23 http://www.chembase.cn/molecule-23.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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
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
IUPAC Traditional name
xanthophyll
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
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
CAS Number
127-40-2
EC Number
204-840-0
PubChem SID
46508835
160963486
PubChem CID
5368396

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
MP Biomedicals
02103292 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 18.217272  H Acceptors
H Donor LogD (pH = 5.5) 8.550209 
LogD (pH = 7.4) 8.550209  Log P 8.550209 
Molar Refractivity 195.0634 cm3 Polarizability 71.71594 Å3
Polar Surface Area 40.46 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 8.29  LOG S -5.89 
Solubility (Water) 7.32e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Insoluble expand Show data source
Hydrophobicity(logP)
7.9 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals
DrugBank - DB00137 external link
Item Information
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
MP Biomedicals - 02103292 external link
Xanthophyll is primarily crystalline lutein obtained from marigold oleoresin and is a 20% suspension in corn oil base.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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