alpha-Carotene (CHEM029033)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:52:35 UTC
Update Date2026-05-14 19:53:32 UTC
Accession NumberCHEM029033
Identification
Common Namealpha-Carotene
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
all-trans-alpha-CaroteneChEBI
all-trans-a-CaroteneGenerator
all-trans-Α-caroteneGenerator
a-CaroteneGenerator
Α-caroteneGenerator
(+)-alpha-CaroteneHMDB
(6'r)-beta,epsilon-CaroteneHMDB
BCRHMDB
beta,epsilon-CaroteneHMDB
Hi-alphaHMDB
alpha-Carotene, (6'r)-isomerHMDB
Chemical FormulaC40H56
Average Molecular Mass536.873 g/mol
Monoisotopic Mass536.438 g/mol
CAS Registry Number7488-99-5
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
Traditional Nameα-carotene
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
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
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability71.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7511590000-5ff377447b1a3120b90bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0434290000-6f904a3c295bc1e6ac54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0957200000-351f26ece1b0df197b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-1868900000-f5489f2f18f85eed5cb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-e93c3c9ed8db3b98e043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-60cec21bb7939f633e51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0947570000-8f7580b6f95f904737f6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003993
FooDB IDFDB013716
Phenol Explorer IDNot Available
KNApSAcK IDC00003765
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6998
PDB IDNot Available
Wikipedia LinkAlpha-Carotene
Chemspider ID3571861
ChEBI ID28425
PubChem Compound ID4369188
Kegg Compound IDC05433
YMDB IDNot Available
ECMDB IDM2MDB005179
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Thomas JB, Kline MC, Schiller SB, Ellerbe PM, Sniegoski LT, Duewer DL, Sharpless KE: Certification of fat-soluble vitamins, carotenoids, and cholesterol in human serum: Standard Reference Material 968b. Anal Bioanal Chem. 1996 Aug;356(1):1-9.
2. Leo MA, Ahmed S, Aleynik SI, Siegel JH, Kasmin F, Lieber CS: Carotenoids and tocopherols in various hepatobiliary conditions. J Hepatol. 1995 Nov;23(5):550-6.
3. Murakoshi M, Nishino H, Satomi Y, Takayasu J, Hasegawa T, Tokuda H, Iwashima A, Okuzumi J, Okabe H, Kitano H, et al.: Potent preventive action of alpha-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by alpha-carotene than by beta-carotene. Cancer Res. 1992 Dec 1;52(23):6583-7.
4. Sommerburg O, Meissner K, Nelle M, Lenhartz H, Leichsenring M: Carotenoid supply in breast-fed and formula-fed neonates. Eur J Pediatr. 2000 Jan-Feb;159(1-2):86-90.
5. Yadav D, Hertan HI, Schweitzer P, Norkus EP, Pitchumoni CS: Serum and liver micronutrient antioxidants and serum oxidative stress in patients with chronic hepatitis C. Am J Gastroenterol. 2002 Oct;97(10):2634-9.
6. Canfield LM, Clandinin MT, Davies DP, Fernandez MC, Jackson J, Hawkes J, Goldman WJ, Pramuk K, Reyes H, Sablan B, Sonobe T, Bo X: Multinational study of major breast milk carotenoids of healthy mothers. Eur J Nutr. 2003 Jun;42(3):133-41.
7. Kontush A, Spranger T, Reich A, Baum K, Beisiegel U: Lipophilic antioxidants in blood plasma as markers of atherosclerosis: the role of alpha-carotene and gamma-tocopherol. Atherosclerosis. 1999 May;144(1):117-22.
8. El-Sohemy A, Baylin A, Kabagambe E, Ascherio A, Spiegelman D, Campos H: Individual carotenoid concentrations in adipose tissue and plasma as biomarkers of dietary intake. Am J Clin Nutr. 2002 Jul;76(1):172-9.
9. Virtanen SM, van't Veer P, Kok F, Kardinaal AF, Aro A: Predictors of adipose tissue carotenoid and retinol levels in nine countries. The EURAMIC Study. Am J Epidemiol. 1996 Nov 15;144(10):968-79.
10. Schmitz HH, Poor CL, Wellman RB, Erdman JW Jr: Concentrations of selected carotenoids and vitamin A in human liver, kidney and lung tissue. J Nutr. 1991 Oct;121(10):1613-21.
11. Forman MR, Beecher GR, Muesing R, Lanza E, Olson B, Campbell WS, McAdam P, Raymond E, Schulman JD, Graubard BI: The fluctuation of plasma carotenoid concentrations by phase of the menstrual cycle: a controlled diet study. Am J Clin Nutr. 1996 Oct;64(4):559-65.
12. Martin KR, Wu D, Meydani M: The effect of carotenoids on the expression of cell surface adhesion molecules and binding of monocytes to human aortic endothelial cells. Atherosclerosis. 2000 Jun;150(2):265-74.
13. Stahl W, Schwarz W, Sies H: Human serum concentrations of all-trans beta- and alpha-carotene but not 9-cis beta-carotene increase upon ingestion of a natural isomer mixture obtained from Dunaliella salina (Betatene). J Nutr. 1993 May;123(5):847-51.
14. Yu MW, Chiang YC, Lien JP, Chen CJ: Plasma antioxidant vitamins, chronic hepatitis B virus infection and urinary aflatoxin B1-DNA adducts in healthy males. Carcinogenesis. 1997 Jun;18(6):1189-94.
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23620017
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24169341
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9408998