Common Name

B-Carotene Description

B-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 usefli for curbing the excess of damaging free radicals in the body. However, the usefliness 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

Synonyms

Value Source 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 Formlia

C40H56 Average Molecliar Weight

536.888 Monoisotopic Molecliar Weight

536.438201803 IUPAC Name

1,3,3-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 Name

β-carotene CAS Registry Number

7235-40-7 SMILES

CC(C=CC=C(/C)C=CC1=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 Key

OENHQHLEOONYIE-JLTXGRSLSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Detected and Quantified Origin

  • Endogenous
  • Food
  • Biofunction

  • Anti-oxidant
  • Cell signaling
  • Component of Retinol metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Application

  • Nutrients
  • Stabilizers
  • Surfactants and Emlisifiers
  • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane (predicted from logP)
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point183 °CNot Available Boiling PointNot AvailableNot Available Water Solubility0.6 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.000391 mg/mLALOGPS logP9.72ALOGPS logP11.12ChemAxon logS-6.1ALOGPS Physiological Charge0ChemAxon Hydrogen Acceptor Count0ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area0 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity191.61 m3·mol-1ChemAxon Polarizability71.84 Å3ChemAxon Number of Rings2ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0016-2794670000-c5bc2a4dbcd0f12cbf7fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0002-2687970000-782d048d873c21fc6b82View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-05ai-1009510000-585581456b10671692bdView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-05mx-2920010000-471219f3e66bafb29beeView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0006-0144900000-2fa7b609c7300ff8aba3View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-05mx-9810010000-9a261fb8602890c2481eView in MoNA 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane (predicted from logP)
  • Biofluid Locations

  • Blood
  • Tissue Location

  • Adipose Tissue
  • Adrenal Gland
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Liver
  • Placenta
  • Platelet
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
  • Pathways

    Name SMPDB Link KEGG Link Retinol MetabolismSMP00074map00830 Vitamin A DeficiencySMP00336Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.82 +/- 0.58 uMChildren (1-13 years old)BothNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified1.59 +/- 0.53 uMAdlit (>18 years old)MaleNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified1.75 +/- 0.64 uMAdlit (>18 years old)FemaleNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified0.56 (0.23-3.92) uMAdolescent (13-18 years old)BothNormal

  • 7657478
  • details BloodDetected and Quantified0.42 (0.19-0.72) uMAdlit (>18 years old)FemaleNormal

  • 19235557
  • details BloodDetected and Quantified1.18 +/- 0.06 uMAdlit (>18 years old)BothNormal

  • 12772433
  • details BloodDetected and Quantified1.01 +/- 0.08 uMAdlit (>18 years old)MaleNormal

  • 12772433
  • details BloodDetected and Quantified1.0 (0.32 – 1.83) uMAdlit (>18 years old)Not SpecifiedNormal

  • 15531679
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.30 (0.15-0.45) uMAdlit (>18 years old)FemaleEndometrial cancer

  • 19235557
  • 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

  • 608089 (Endometrial cancer)
  • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB014613 KNApSAcK ID

    C00000919 Chemspider ID

    4444129 KEGG Compound ID

    C02094 BioCyc ID

    CPD1F-129 BiGG ID

    2264935 Wikipedia Link

    Betacarotene NuGOwiki Link

    HMDB00561 Metagene Link

    HMDB00561 METLIN ID

    5545 PubChem Compound

    5280489 PDB ID

    BCR ChEBI ID

    17579

    Product: Emetine (dihydrochloride hydrate)

    References Synthesis Reference Not 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 ]
    18. Metnitz GH, Fischer M, Bartens C, Steltzer H, Lang T, Druml W: Impact of acute renal failure on antioxidant status in multiple organ failure. Acta Anaesthesiol Scand. 2000 Mar;44(3):236-40. [PubMed:10714834 ]
    19. Zhou JF, Chen P, Yang JL, Zhu YG, Peng CH, Wu YL: Oxidative stress before and after operation in patients with chronic cholecystitis containing gallstone. Biomed Environ Sci. 2000 Dec;13(4):254-62. [PubMed:11351858 ]
    20. Dimenstein R, Trugo NM, Donangelo CM, Trugo LC, Anastacio AS: Effect of subadequate maternal vitamin-A status on placental transfer of retinol and beta-carotene to the human fetus. Biol Neonate. 1996;69(4):230-4. [PubMed:8724650 ]

    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 → Retinal details B-Carotene + Oxygen + Reduced acceptor → beta-Carotene-15,15'-epoxide + Water + Acceptor details
    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-Ionone details

    PMID: 22580348