Record Information
Version1.0
Creation date2010-04-08 22:10:52 UTC
Update date2019-11-27 17:25:03 UTC
Primary IDFDB013716
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Carotene
DescriptionWidespread carotenoid, e.g. in carrots and palm oil. Has vitamin A activity but less than that of b-Carotene Apha-carotene is one of the primary isomer of carotene. plasma levels of alpha-carotene is positively associated with the detection rate of (theaflatoxin B1)AFB1-DNA adducts in a dose-dependent manner, whereas plasma lycopene level was inversely related to the presence of the adducts in urine.(PMID: 9214602). alpha-Carotene is found in many foods, some of which are cloves, shallot, cumin, and potato.
CAS Number7488-99-5
Structure
Thumb
Synonyms
SynonymSource
(+)-alpha-CaroteneChEBI
alpha-Carotene (natural)ChEBI
(+)-a-CaroteneGenerator
(+)-α-caroteneGenerator
a-CaroteneGenerator
α-caroteneGenerator
a-Carotene (natural)Generator
α-carotene (natural)Generator
CarotenesMeSH
CarotenoidsMeSH
alpha-Carotene, (6'r)-isomerMeSH
(6'R)-beta,epsilon-Carotenebiospider
(R)-alpha-Carotenedb_source
4',5'-Didehydro-5',6'-dihydro-beta,beta-carotenebiospider
all-trans-a-CaroteneGenerator
all-trans-alpha-Carotenebiospider
all-trans-α-caroteneGenerator
alpha-Carotenebiospider
BCRHMDB
beta,epsilon-Carotenebiospider
Hi-alphaHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00031 g/LALOGPS
logP9.79ALOGPS
logP11.17ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.88 m³·mol⁻¹ChemAxon
Polarizability72.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56
IUPAC name(6R)-1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
InChI IdentifierInChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1
InChI KeyANVAOWXLWRTKGA-NTXLUARGSA-N
Isomeric SMILESC/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)/C=C/C=C(\C)/C=C/[C@H]1C(C)=CCCC1(C)C
Average Molecular Weight536.8726
Monoisotopic Molecular Weight536.438201792
Classification
DescriptionThis compound belongs to the class of chemical entities known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentCarotenes
Alternative Parents
Substituents
  • Carotene
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Foods

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 89.49%; H 10.51%DFC
Melting PointMp 187°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18643 +385 (C6H6)DFC
Spectroscopic UV Data471 () (hexane)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0334190000-e05f79db2e425bfe8186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0769200000-81f1f88961c73bc3943aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-2689700000-a8528456aa6fa28bfb10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-df0db1851156c1e36da6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-ac5ac3829642d0394d24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0947360000-b2ba5d2cce5367c8424bView in MoNA
ChemSpider ID3571861
ChEMBL IDNot Available
KEGG Compound IDC05433
Pubchem Compound ID4369188
Pubchem Substance IDNot Available
ChEBI ID35147
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03993
CRC / DFC (Dictionary of Food Compounds) IDHVF46-E:JGG21-T
EAFUS IDNot Available
Dr. Duke IDALPHA-CAROTENE|BETA-EPSILON-CAROTENE
BIGG IDNot Available
KNApSAcK IDC00003765
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAlpha-Carotene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proliferantDUKE
colorant37958 DUKE
provitamin A50188 A substance that can be converted into a vitamin by animal tissues.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.