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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 08:42:22 UTC
Update Date2019-01-11 19:17:51 UTC
HMDB IDHMDB0003993
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 ).
Structure
Data?1547234271
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 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
SMILES
C\C(\C=C\C=C(/C)\C=C\C1C(C)=CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=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+
InChI KeyANVAOWXLWRTKGA-JLTXGRSLSA-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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7511590000-5ff377447b1a3120b90bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0434290000-6f904a3c295bc1e6ac54JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0957200000-351f26ece1b0df197b1aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-1868900000-f5489f2f18f85eed5cb1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-e93c3c9ed8db3b98e043JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-60cec21bb7939f633e51JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0947570000-8f7580b6f95f904737f6JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue Locations
  • Adipose Tissue
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.05 +/- 0.04 uMAdolescent (13-18 years old)Female
Normal
details
BloodDetected and Quantified0.04 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.06 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.031 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.208 +/- 0.00600 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0500 +/- 0.0500 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0400 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0600 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0960 +/- 0.140 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.117 +/- 0.0870 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0610 +/- 0.0700 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0500 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0600 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0820 +/- 0.0530 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.140 +/- 0.230 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.150 +/- 0.130 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.110 +/- 0.120 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0987 +/- 0.0801 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.180 +/- 0.200 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.190 +/- 0.190 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.1 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified3.25 (0.90-5.60) uMAdult (>18 years old)Not SpecifiedNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.07 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified110 +/- 80 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0913 +/- 0.0708 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0800 +/- 0.0500 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0555 +/- 0.0669 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.07 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.08 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.051 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.146 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.514 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.601 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.12 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.238 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.282 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.098 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0986 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.112 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0400 +/- 0.0200 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0500 +/- 0.0300 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0764 +/- 0.121 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0969 +/- 0.0782 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.104 +/- 0.0801 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.110 +/- 0.0800 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.120 +/- 0.110 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.07 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.108 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.11 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.11 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.13 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.2 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0736 +/- 0.0514 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0820 +/- 0.0894 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.104 +/- 0.0857 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.117 +/- 0.0913 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.120 +/- 0.0900 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.120 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.140 +/- 0.0700 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.180 +/- 0.151 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified124.980 +/- 97.599 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified186.259 +/- 93.129 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.07 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.08 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.093 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.117 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.12 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0503 +/- 0.0373 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0503 +/- 0.0484 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0689 +/- 0.0428 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0689 +/- 0.0894 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0810 +/- 0.0600 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0880 +/- 0.0730 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0911 +/- 0.0577 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.110 +/- 0.100 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.120 +/- 0.0600 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.135 +/- 0.0920 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified113.990 +/- 103.187 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified70 +/- 60 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified90 +/- 70 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified130.381 +/- 74.503 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.120 +/- 0.0900 uMChildren (1 - 13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.11 +/- 0.09 uMAdult (>18 years old)BothNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0590 +/- 0.0500 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.0770 +/- 0.0800 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified71000 uMAdult (>18 years old)Both
Colorectal, breast, or neuroendocrine cancer
details
BloodDetected and Quantified0.0800 +/- 0.0700 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.0500 +/- 0.0400 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.0800 +/- 0.0600 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
BloodDetected and Quantified0.12 +/- 0.11 uMAdult (>18 years old)BothAfter tomato drink intake details
Associated Disorders and Diseases
Disease References
Obesity
  1. Vioque J, Weinbrenner T, Asensio L, Castello A, Young IS, Fletcher A: Plasma concentrations of carotenoids and vitamin C are better correlated with dietary intake in normal weight than overweight and obese elderly subjects. Br J Nutr. 2007 May;97(5):977-86. [PubMed:17408529 ]
  2. Burrows TL, Warren JM, Colyvas K, Garg ML, Collins CE: Validation of overweight children's fruit and vegetable intake using plasma carotenoids. Obesity (Silver Spring). 2009 Jan;17(1):162-8. doi: 10.1038/oby.2008.495. Epub 2008 Nov 6. [PubMed:18997681 ]
Diabetes mellitus type 1
  1. Granado-Lorencio F, Olmedilla-Alonso B, Blanco-Navarro I, Botella-Romero F, Simal-Anton A: Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up study. Eur J Clin Nutr. 2006 Aug;60(8):1000-8. Epub 2006 Feb 1. [PubMed:16452910 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013716
KNApSAcK IDC00003765
Chemspider ID3571861
KEGG Compound IDC05433
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Carotene
METLIN ID6998
PubChem Compound4369188
PDB IDNot Available
ChEBI ID28425
References
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 ]