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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H56O2
Molecular Weight 568.8714
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 9
Charge 0

SHOW SMILES / InChI
Structure of LUTEIN

SMILES

CC(\C=C\C=C(C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C

InChI

InChIKey=KBPHJBAIARWVSC-RGZFRNHPSA-N
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+/t35-,36+,37-/m0/s1

HIDE SMILES / InChI

Molecular Formula C40H56O2
Molecular Weight 568.8714
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 9
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00137 and http://www.ncbi.nlm.nih.gov/pubmed/26798505

Lutein is a xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis. Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance. Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation. 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). There is also epidemiological evidence that increasing lutein and zeaxanthin intake lowers the risk of cataract development. Consumption of more than 2.4 mg of lutein/zeaxanthin daily from foods and supplements was significantly correlated with reduced incidence of nuclear lens opacities, as revealed from data collected during a 13- to 15-year period in the Nutrition and Vision Project (NVP).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P22309
Gene ID: 54658.0
Gene Symbol: UGT1A1
Target Organism: Homo sapiens (Human)
45.5 µM [IC50]
Target ID: P22310
Gene ID: 54657.0
Gene Symbol: UGT1A4
Target Organism: Homo sapiens (Human)
28.7 µM [IC50]
10.9 µM [IC50]
2.5 µM [IC50]
Target ID: Plasmodium falciparum (D10)
12.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Advances in the researches of lutein and alzheimer's disease].
2015 May
In Vitro Inhibition of Human UDP-Glucuronosyl-Transferase (UGT) Isoforms by Astaxanthin, β-Cryptoxanthin, Canthaxanthin, Lutein, and Zeaxanthin: Prediction of in Vivo Dietary Supplement-Drug Interactions.
2016 Aug 12
The effects of lutein on cardiometabolic health across the life course: a systematic review and meta-analysis.
2016 Feb
Phytochemical Analysis with Antioxidant and Cytotoxicity Studies of the Bioactive Principles from Zanthoxylum capense (Small Knobwood).
2017
Patents

Sample Use Guides

In Vivo Use Guide
Take two capsules of VISUtein per day with a meal. VISUtein provides 18 mg of lutein, along with 200 mg of N-acetyl cystein, and 60 mg anthocyanidins from bilberry. Other ingredients are mixed carotenoids, vitamins A, B2, and zinc.
Route of Administration: Oral
In Vitro Use Guide
Lutein exhibited antiplasmodial activity against the chloroquine-sensitive strain of Plasmodium falciparum (D10) with IC50 12.5 uM
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:44:12 UTC 2023
Edited
by admin
on Fri Dec 15 15:44:12 UTC 2023
Record UNII
X72A60C9MT
Record Status Validated (UNII)
Record Version
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Name Type Language
LUTEIN
DSC   FCC   MART.   USP-RS   VANDF  
Common Name English
INS NO.161B(I)
Code English
.BETA.,.BETA.-CAROTENE-3,3'-DIOL, 4,5-DIDEHYDRO-5,6-DIHYDRO-, (3R,3'R,6R)-
Common Name English
.BETA.,.EPSILON.-CAROTENE-3,3'-DIOL
Common Name English
VEGETABLE LUTEIN
Common Name English
E 161
Code English
NSC-59193
Code English
INS-161B(I)
Code English
XANTOFYL
WHO-DD  
Common Name English
Xantofyl [WHO-DD]
Common Name English
E 161B
Common Name English
LUTEIN [VANDF]
Common Name English
OS 24
Common Name English
LUTEIN [FCC]
Common Name English
LUTEIN [DSC]
Common Name English
FLORAGLO
Common Name English
LUTEIN A
Common Name English
LEUTEIN [VANDF]
Common Name English
(3R,3'R,6R)-4,5-DIDEHYDRO-5,6-DIHYDRO-.BETA.,.BETA.-CAROTENE-3,3'-DIOL
Common Name English
.BETA.,.EPSILON.-CAROTENE-3,3'-DIOL, (3R,3'R,6'R)-
Common Name English
FLORAGLO LUTEIN
Common Name English
XANTHOPHYLL [MI]
Common Name English
ORO GLO 7
Common Name English
XANTHOPHYLL
MI  
Common Name English
TRANS-LUTEIN
Common Name English
(1R,4R)-4-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((4R)-4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-3,7,12,16-TETRAMETHYL-1,3,5,7,9,11,13,15,17-OCTADECANONAEN-1-YL)-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-OL
Common Name English
ALL-TRANS-XANTHOPHYLL
Common Name English
LUTEIN [MART.]
Common Name English
(3R,3'R,6R)-4,5-DIDEHYDRO-5,6-DIHYDRO-.BETA.,.BETA.-CAROTIN-3,3'-DIOL
Common Name English
VEGETABLE LUTEOL
Common Name English
E-161B(I)
Code English
ALL-TRANS-LUTEIN
Common Name English
LUTEIN FROM TAGETES ERECTA
Common Name English
BO-XAN
Common Name English
LUTEIN [USP-RS]
Common Name English
E-161B
Code English
Classification Tree Code System Code
JECFA EVALUATION INS-161B(I)
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
DSLD 166 (Number of products:2293)
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
NCI_THESAURUS C68307
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-161B(I)
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
Code System Code Type Description
WIKIPEDIA
LUTEIN
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
CHEBI
28838
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
SMS_ID
100000088311
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
FDA UNII
X72A60C9MT
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
DRUG CENTRAL
4145
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
291
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
542
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
DRUG BANK
DB00137
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
PUBCHEM
5281243
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
390
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
MERCK INDEX
m11531
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY Merck Index
MESH
D014975
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
NCI_THESAURUS
C1965
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-840-0
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
RXCUI
11359
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY RxNorm
NSC
59193
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046749
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
EVMPD
SUB20713
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
DAILYMED
X72A60C9MT
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
140
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
385
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
CAS
127-40-2
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
221
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1370804
Created by admin on Fri Dec 15 15:44:12 UTC 2023 , Edited by admin on Fri Dec 15 15:44:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
page 594
PARENT -> CONSTITUENT ALWAYS PRESENT
page 594
PARENT -> CONSTITUENT MAY BE PRESENT
9.0% total carotenoid content
USP
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
Unit: ng/g; The content of carotenoids from selected commercially available health supplements (Spirulina)
ASSAY (HPLC)
Batch Data
Related Record Type Details
IMPURITY -> PARENT
USP
Related Record Type Details
ACTIVE MOIETY