CHEBI:27740 - γ-carotene

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ChEBI Name γ-carotene
ChEBI ID CHEBI:27740
ChEBI ASCII Name gamma-carotene
Definition A cyclic carotene obtained by the cyclisation of lycopene.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24189, CHEBI:10560
Supplier Information ZINC000001532567
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β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons. Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A). In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato. It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity. β-carotene is the most common carotenoid in plants. When used as a food coloring, it has the E number E160a.: 119  The structure was deduced in 1930. Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It is industrially extracted from richer sources such as the algae Dunaliella salina. The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane. Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic.
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Formula C40H56
Net Charge 0
Average Mass 536.87264
Monoisotopic Mass 536.43820
InChI InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
InChIKey HRQKOYFGHJYEFS-BXOLYSJBSA-N
SMILES CC(C)=CCC\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\C1=C(C)CCCC1(C)C
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing γ-carotene (CHEBI:27740) has role fungal metabolite (CHEBI:76946)
γ-carotene (CHEBI:27740) has role plant metabolite (CHEBI:76924)
γ-carotene (CHEBI:27740) is a carotenoid β-end derivative (CHEBI:139120)
γ-carotene (CHEBI:27740) is a cyclic carotene (CHEBI:35163)
Incoming 1'-hydroxy-γ-carotene (CHEBI:80133) has parent hydride γ-carotene (CHEBI:27740)
rubixanthin (CHEBI:8907) has parent hydride γ-carotene (CHEBI:27740)
IUPAC Name
β,ψ-carotene
Synonyms Sources
gamma-Carotene KEGG COMPOUND
γ-carotene UniProt
Manual Xrefs Databases
C00000926 KNApSAcK
C05435 KEGG COMPOUND
CPD1F-126 MetaCyc
Gamma-carotene Wikipedia
LMPR01070260 LIPID MAPS
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Registry Numbers Types Sources
2066713 Reaxys Registry Number Reaxys
472-93-5 CAS Registry Number ChemIDplus
Citations Types Sources
13114888 PubMed citation Europe PMC
14817276 PubMed citation Europe PMC
17992006 PubMed citation Europe PMC
23412054 PubMed citation Europe PMC
4784609 PubMed citation Europe PMC
Last Modified
05 February 2019