CAS 127-40-2|trans-Lutein|Lutein|beta,epsilon-Carotene-3,3'-diol|All-trans-Lutein|Phylloxanthin|4,5-Didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diol|4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydro...

General Information

Structure

Molecular Formula

C₄₀H₅₆O₂

Molecular Mass

568.87144

Exact Mass

568.42803103

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

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

Polarizability

71.71594

Polar Surface Area

40.46

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

8.29

LOG S

-5.89

Solubility (Water)

7.32e-04 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

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

Synonyms

(3R,3'R,6'R)-LuteinCarotenoidAll-trans-(+)-XanthophyllPhylloxanthin(3R,3'R)-Beta,Beta-Carotene-3,3'-Diol, Lutein4,5-Didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diolbeta,epsilon-Carotene-3,3'-diolLuteineLutein esterLuteinVegetable luteintrans-LuteinVegetable luteolAll-trans-Lutein(3R,3'R,6S)-4,5-Didehydro-5,6-Dihydro-Beta,Beta-Carotene-3,3'-Diolall-trans-XanthophyllXanthophyll

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

Brand Name

Bo-Xan

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem CID

PubChem SID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

7.9

Solubility

Insoluble

Safety Information

MSDS Link

Download link

Storage Condition

Room Temperature (15-30°C)

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

MP Biomedicals

02103292

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

Molecule Details