ChemFOnt: Showing chemical card for Lutein ester (CFc000282529)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:58 UTC

Chemfont ID

CFc000282529

Molecule Identification

Common Name

Lutein ester

Definition

Lutein, also known as all-trans-lutein or 3,3'-dihydroxy-alpha-carotene, is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Lutein is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Lutein can be found in dandelion and ginkgo nuts, which makes lutein a potential biomarker for the consumption of these food products. Lutein can be found primarily in blood, as well as throughout most human tissues. Lutein exists in all eukaryotes, ranging from yeast to humans. Lutein is isomeric with zeaxanthin, differing only in the placement of one double bond. Lutein and zeaxanthin can be interconverted in the body through an intermediate called meso-zeaxanthin. The principal natural stereoisomer of lutein is (3R,3‚Ä≤R,6‚Ä≤R)-beta,epsilon-carotene-3,3‚Ä≤-diol. Lutein is a lipophilic molecule and is generally insoluble in water. The presence of the long chromophore of conjugated double bonds (polyene chain) provides the distinctive light-absorbing properties. The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,3'-Dihydroxy-alpha-carotene	HMDB
all-trans-(+)-Xanthophyll	HMDB
all-trans-Lutein	HMDB
beta,epsilon-Carotene-3,3'-diol	HMDB
bo-Xan	HMDB
Lutein ester	HMDB
Luteine	HMDB
trans-Lutein	HMDB
Vegetable lutein	HMDB
Vegetable luteol	HMDB
Lutein F	MeSH, HMDB
Lutein g	MeSH, HMDB
Lutein, gamma	MeSH, HMDB
gamma Lutein	MeSH, HMDB

Chemical Formula

C₄₀H₅₆O₂

Average Molecular Weight

568.8714

Monoisotopic Molecular Weight

568.428031036

IUPAC Name

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-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

Traditional Name

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-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

CAS Registry Number

127-40-2

SMILES

O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1

InChI Identifier

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+/m1/s1

InChI Key

KBPHJBAIARWVSC-RTIVXWJOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cell

Fibroblast

Fibroblast (HMDB: HMDB0303013)

Nerve cell (HMDB: HMDB0303013)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0303013)

Tissue

Connective tissue

Adipose tissue (HMDB: HMDB0303013)

Epithelium

Epidermis (HMDB: HMDB0303013)

Organ

Gland

Adrenal Gland (HMDB: HMDB0303013)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0303013)

Source

Exogenous

Exogenous (HMDB: HMDB0303013)

Food

Food (HMDB: HMDB0303013)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Fruit

Fruits (HMDB: HMDB0303013)

Vegetable

Vegetables (HMDB: HMDB0303013)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0303013)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0303013)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0303013)

Lipid metabolism pathway (HMDB: HMDB0303013)

Cellular process

Cell signaling (HMDB: HMDB0303013)

Biochemical process

Lipid transport (HMDB: HMDB0303013)

Role

Biological role

Energy source (HMDB: HMDB0303013)

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0303013)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0303013)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00073 g/L	ALOGPS
logP	8.29	ALOGPS
logP	8.55	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	195.06 m³·mol⁻¹	ChemAxon
Polarizability	73.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303013

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007276

KNApSAcK ID

C00003774

Chemspider ID

4938343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6433159

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Lutein ester (CFc000282529)

MOL for CFc000282529 (Lutein ester)

3D MOL for CFc000282529 (Lutein ester)

3D SDF for CFc000282529 (Lutein ester)

3D-SDF for CFc000282529 (Lutein ester)

PDB for CFc000282529 (Lutein ester)

3D PDB for CFc000282529 (Lutein ester)

SMILES for CFc000282529 (Lutein ester)

INCHI for CFc000282529 (Lutein ester)

Structure for CFc000282529 (Lutein ester)

3D Structure for CFc000282529 (Lutein ester)