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Record Information
Creation Date2006-08-13 08:42:22 UTC
Update Date2017-08-16 04:14:00 UTC
Secondary Accession Numbers
  • HMDB03993
Metabolite Identification
Common NameAlpha-Carotene
DescriptionApha-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, (6'r)-isomerMeSH
Chemical FormulaC40H56
Average Molecular Weight536.888
Monoisotopic Molecular Weight536.438201803
IUPAC Name1,5,5-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
CAS Registry Number7488-99-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Carotene
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting Point187.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.000307 mg/mLALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.88 m3·mol-1ChemAxon
Polarizability71.27 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Liver
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.05 +/- 0.04 uMAdolescent (13-18 years old)Female
BloodDetected and Quantified3.25 (0.90-5.60) uMAdult (>18 years old)Not SpecifiedNormal
    • The Merck Manual,...
BloodDetected and Quantified0.11 +/- 0.09 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.12 +/- 0.11 uMAdult (>18 years old)BothAfter tomato drink intake details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013716
KNApSAcK IDC00003765
Chemspider ID3571861
KEGG Compound IDC05433
BioCyc IDCPD1F-118
BiGG IDNot Available
Wikipedia LinkBCR
NuGOwiki LinkHMDB0003993
PubChem Compound4369188
PDB IDNot Available
ChEBI ID28425
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:12081831 ]
  2. 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. [PubMed:10381285 ]
  3. 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. [PubMed:15045249 ]
  4. 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. [PubMed:8583143 ]
  5. 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. [PubMed:1423303 ]
  6. 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. [PubMed:10653337 ]
  7. 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. [PubMed:12385452 ]
  8. 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. [PubMed:12811470 ]
  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. [PubMed:8916508 ]
  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. [PubMed:1765826 ]
  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. [PubMed:8839500 ]
  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. [PubMed:10856518 ]
  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. [PubMed:8487096 ]
  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. [PubMed:9214602 ]