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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:52:48 UTC
HMDB IDHMDB0000561
Secondary Accession Numbers
  • HMDB00561
Metabolite Identification
Common NameB-Carotene
DescriptionB-Carotene is a carotenoid that is a precursor of vitamin A. It is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (porphyria, erythropoietic). (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Engewood, CO, 1995.) -- Pubchem; Carotene is an orange photosynthetic pigment important for photosynthesis. It is responsible for the orange colour of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol (vitamin A) and comes in two primary forms: alpha- and beta-carotene. gamma-, delta- and epsilon-carotene also exist. Carotene can be stored in the liver and converted to vitamin A as needed. Beta-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of beta-carotene as a dietary supplement (i.e. taken as a pill) is still subject to debate. Beta-carotene is fat-soluble, so a small amount of fat is needed to absorb it into the body. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene)ChEBI
all-trans-beta-CaroteneChEBI
beta-KarotinChEBI
all-trans-b-CaroteneGenerator
all-trans-β-caroteneGenerator
b-KarotinGenerator
β-karotinGenerator
(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bisHMDB
(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-cyclohexeneHMDB
all-e-b-CaroteneHMDB
all-epsilon-beta-CaroteneHMDB
beta-CaroteneHMDB
BetacaroteneHMDB
BetaVitHMDB
CarotabenHMDB
Carotene base 80SHMDB
FOOD Orange 5HMDB
KPMKHMDB
LucaratinHMDB
LucarotinHMDB
LurotinHMDB
ProvateneHMDB
ProvatenolHMDB
Rovimix b-caroteneHMDB
SerlaboHMDB
SolateneHMDB
Hermal brand OF betacaroteneMeSH
Max-caroMeSH
Merck brand OF betacaroteneMeSH
Roche brand OF betacaroteneMeSH
BellaCarotinMeSH
Betacarotene roche brandMeSH
Betacarotene solgar brandMeSH
Marlyn brand OF betacaroteneMeSH
Betacarotene hermal brandMeSH
Max caroMeSH
Solgar brand OF betacaroteneMeSH
3m Brand OF betacaroteneMeSH
Betacarotene 3m brandMeSH
Betacarotene marlyn brandMeSH
Betacarotene merck brandMeSH
Carotene, betaMeSH
MaxCaroMeSH
VetoronMeSH
beta CaroteneMeSH
Chemical FormulaC40H56
Average Molecular Weight536.888
Monoisotopic Molecular Weight536.438201803
IUPAC Name1,3,3-trimethyl-2-[(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 Nameβ-carotene
CAS Registry Number7235-40-7
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(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/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+
InChI KeyOENHQHLEOONYIE-JLTXGRSLSA-N
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
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
Physiological effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Cell:

    Element:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.6 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00039 g/LALOGPS
logP9.72ALOGPS
logP11.12ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.61 m³·mol⁻¹ChemAxon
Polarizability71.84 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3211290000-f968c686d39ae0f0fc50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0016-2794670000-c5bc2a4dbcd0f12cbf7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-2687970000-782d048d873c21fc6b82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05ai-1009510000-585581456b10671692bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-05mx-2920010000-471219f3e66bafb29beeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0144900000-2fa7b609c7300ff8aba3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0434190000-0f2f0f2c4af76e6c3322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0679100000-6f4450c8ade1963f9201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-1789100000-6f2a7024e42303e7737aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-cdea7c2d939f0c68b905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-530c81799c9daabdc9bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0968170000-ec71ee19e546088e3b05View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05mx-9810010000-9a261fb8602890c2481eView in MoNA
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Liver
  • Placenta
  • Platelet
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
Pathways
NameSMPDB/PathwhizKEGG
Retinol MetabolismPw000164Pw000164 greyscalePw000164 simpleMap00830
Vitamin A DeficiencyPw000210Pw000210 greyscalePw000210 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.133 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.936 +/- 0.0300 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.420 +/- 0.330 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.450 +/- 0.250 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.460 +/- 0.220 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.480 +/- 0.250 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.304 +/- 0.340 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.400 +/- 0.210 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.400 +/- 0.210 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.510 +/- 0.340 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.196 +/- 0.230 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.330 +/- 0.230 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.510 +/- 0.380 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.520 +/- 0.480 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.82 +/- 0.58 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.393 +/- 0.530 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified1.59 +/- 0.53 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.653 +/- 0.355 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.75 +/- 0.64 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.391 +/- 0.215 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.685 +/- 0.404 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.440 +/- 0.251 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.560 +/- 0.440 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.410 +/- 0.340 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.460 +/- 0.304 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.580 +/- 0.480 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.640 +/- 0.440 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.26 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.21 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified340 +/- 190 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.421 +/- 0.253 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.260 +/- 0.120 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.230 +/- 0.120 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.213 +/- 0.190 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.31 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.33 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.19 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.748 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.391 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.4 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.844 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.943 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.071 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.56 (0.23-3.92) uMAdolescent (13-18 years old)BothNormal details
BloodDetected and Quantified0.414 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.501 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.528 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.83 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.84 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.85 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.89 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.198 +/- 0.150 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.292 +/- 0.218 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.370 +/- 0.290 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.400 +/- 0.340 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.410 +/- 0.270 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.420 +/- 0.340 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.430 +/- 0.360 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.440 +/- 0.471 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.450 +/- 0.290 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.451 +/- 0.292 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.490 +/- 0.380 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.530 +/- 0.350 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.540 +/- 0.340 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.620 +/- 0.590 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.728 +/- 0.358 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantifiedv +/- 0.120 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.333 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.374 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.44 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.536 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.54 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.71 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.72 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.302 +/- 0.184 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.373 +/- 0.319 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.397 +/- 0.384 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.406 +/- 0.345 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.471 +/- 0.309 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.542 +/- 0.270 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.580 +/- 0.370 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.581 +/- 0.311 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.600 +/- 0.500 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.821 +/- 0.725 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified574.980 +/- 375.125 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1061.674 +/- 689.157 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.307 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.33 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.36 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.434 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.48 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.62 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.209 +/- 0.184 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.240 +/- 0.152 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.244 +/- 0.207 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.251 +/- 0.212 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.257 +/- 0.235 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.283 +/- 0.143 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.357 +/- 0.285 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.449 +/- 0.230 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.460 +/- 0.290 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.470 +/- 0.330 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.484 +/- 0.407 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified350 +/- 150 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified459.500 +/- 290.191 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified580 +/- 300 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified596.0275 +/- 447.0206 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.590 +/- 0.440 uMChildren (1 - 13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.42 (0.19-0.72) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.18 +/- 0.06 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.01 +/- 0.08 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.0 (0.32 - 1.83) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.23 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.28 uMAdult (>18 years old)Both
Normal
details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.201 +/- 0.180 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.249 +/- 0.250 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified277000 uMAdult (>18 years old)Both
Colorectal, breast, or neuroendocrine cancer
details
BloodDetected and Quantified0.390 +/- 0.260 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.200 +/- 0.130 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.330 +/- 0.190 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
BloodDetected and Quantified0.30 (0.15-0.45) uMAdult (>18 years old)FemaleEndometrial cancer details
Associated Disorders and Diseases
Disease References
Endometrial cancer
  1. Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. doi: 10.1080/00016340902767187. [PubMed:19235557 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014613
KNApSAcK IDC00000919
Chemspider ID4444129
KEGG Compound IDC02094
BioCyc IDCPD1F-129
BiGG ID2264935
Wikipedia LinkBetacarotene
METLIN ID5545
PubChem Compound5280489
PDB IDBCR
ChEBI ID17579
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rushin WG, Catignani GL, Schwartz SJ: Determination of beta-carotene and its cis isomers in serum. Clin Chem. 1990 Nov;36(11):1986-9. [PubMed:2242585 ]
  2. Vahlquist A, Lee JB, Michaelsson G, Rollman O: Vitamin A in human skin: II Concentrations of carotene, retinol and dehydroretinol in various components of normal skin. J Invest Dermatol. 1982 Aug;79(2):94-7. [PubMed:7097042 ]
  3. Bacic-Vrca V, Skreb F, Cepelak I, Mayer L, Kusic Z, Petres B: The effect of antioxidant supplementation on superoxide dismutase activity, Cu and Zn levels, and total antioxidant status in erythrocytes of patients with Graves' disease. Clin Chem Lab Med. 2005;43(4):383-8. [PubMed:15899653 ]
  4. Wu K, Erdman JW Jr, Schwartz SJ, Platz EA, Leitzmann M, Clinton SK, DeGroff V, Willett WC, Giovannucci E: Plasma and dietary carotenoids, and the risk of prostate cancer: a nested case-control study. Cancer Epidemiol Biomarkers Prev. 2004 Feb;13(2):260-9. [PubMed:14973107 ]
  5. Huang C, Tang YL, Chen CY, Chen ML, Chu CH, Hseu CT: The bioavailability of beta-carotene in stir- or deep-fried vegetables in men determined by measuring the serum response to a single ingestion. J Nutr. 2000 Mar;130(3):534-40. [PubMed:10702581 ]
  6. Gerber M: Qualitative methods to evaluate Mediterranean diet in adults. Public Health Nutr. 2006 Feb;9(1A):147-51. [PubMed:16512962 ]
  7. 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 ]
  8. Gollnick HP, Siebenwirth C: Beta-carotene plasma levels and content in oral mucosal epithelium is skin type associated. Skin Pharmacol Appl Skin Physiol. 2002 Sep-Oct;15(5):360-6. [PubMed:12239432 ]
  9. Lee J, Jiang S, Levine N, Watson RR: Carotenoid supplementation reduces erythema in human skin after simulated solar radiation exposure. Proc Soc Exp Biol Med. 2000 Feb;223(2):170-4. [PubMed:10654620 ]
  10. Stahl W, Schwarz W, Sundquist AR, Sies H: cis-trans isomers of lycopene and beta-carotene in human serum and tissues. Arch Biochem Biophys. 1992 Apr;294(1):173-7. [PubMed:1550343 ]
  11. Stahl W, Heinrich U, Jungmann H, Sies H, Tronnier H: Carotenoids and carotenoids plus vitamin E protect against ultraviolet light-induced erythema in humans. Am J Clin Nutr. 2000 Mar;71(3):795-8. [PubMed:10702175 ]
  12. Chanarat N, Chanarat P, Viratsethasin K, Suttajit M, Chiewsilp D: Biochemical and hematological manifestations of HIV/AIDS in Chiang Mai, Thailand. Southeast Asian J Trop Med Public Health. 2001 Sep;32(3):500-3. [PubMed:11944706 ]
  13. Heinrich U, Gartner C, Wiebusch M, Eichler O, Sies H, Tronnier H, Stahl W: Supplementation with beta-carotene or a similar amount of mixed carotenoids protects humans from UV-induced erythema. J Nutr. 2003 Jan;133(1):98-101. [PubMed:12514275 ]
  14. Poor CL, Bierer TL, Merchen NR, Fahey GC Jr, Murphy MR, Erdman JW Jr: Evaluation of the preruminant calf as a model for the study of human carotenoid metabolism. J Nutr. 1992 Feb;122(2):262-8. [PubMed:1732467 ]
  15. Lakshman MR: Alpha and omega of carotenoid cleavage. J Nutr. 2004 Jan;134(1):241S-245S. [PubMed:14704327 ]
  16. Kirsh VA, Hayes RB, Mayne ST, Chatterjee N, Subar AF, Dixon LB, Albanes D, Andriole GL, Urban DA, Peters U: Supplemental and dietary vitamin E, beta-carotene, and vitamin C intakes and prostate cancer risk. J Natl Cancer Inst. 2006 Feb 15;98(4):245-54. [PubMed:16478743 ]
  17. McArdle F, Rhodes LE, Parslew RA, Close GL, Jack CI, Friedmann PS, Jackson MJ: Effects of oral vitamin E and beta-carotene supplementation on ultraviolet radiation-induced oxidative stress in human skin. Am J Clin Nutr. 2004 Nov;80(5):1270-5. [PubMed:15531675 ]
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Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:
BCMO1
Uniprot ID:
Q9HAY6
Molecular weight:
62636.69
Reactions
B-Carotene + Oxygen → Retinaldetails
B-Carotene + Oxygen + Reduced acceptor → beta-Carotene-15,15'-epoxide + Water + Acceptordetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Asymmetrically cleaves beta-carotene at the 9',10' double bond resulting in the formation of beta-apo-10'-carotenal and beta-ionone. Besides beta-carotene, lycopene is also oxidatively cleaved. The apocarotenals formed by this enzyme may be the precursors for the biosynthesis of retinoic acid or exert unknown physiological effects.
Gene Name:
BCO2
Uniprot ID:
Q9BYV7
Molecular weight:
61509.65
Reactions
B-Carotene + Oxygen → all-trans-10'-apo-beta-carotenal + beta-Iononedetails