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Entry
CA00587                                                            

Classification
Carotenoid Name
α-Carotene;
alpha-Carotene;
(6'R)-α-Carotene
IUPAC name (6'R)-beta,epsilon-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Provitamin A activity - 30-50% of all-trans-β-carotene (Ref.408, Ref.467).
  • Anticarcinogenic activity - stronger than β-carotene (Ref.418, Ref.411, Ref.414, Ref.491).
  • An antioxidant - 87.5 times stronger singlet oxygen quenching ability than that ofα-tocopherol - SOAC value: 87.5±2.7 (Ref.616, Ref.597, Ref.598, Ref.599, Ref.415).
  • Number of
    conjugated double bonds 
    10
    Number of
    conjugated multiple bonds 
    10
    Isomers 
  • Constitutional isomer: CA00043, CA00045, CA00191, CA00298, CA00305, CA00309, CA00677, CA00680, CA00681, CA00720
  • Enantiomer: CA01191
  • InChI
    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+/t37-/m0/s1
    InChIKey
    ANVAOWXLWRTKGA-NTXLUARGSA-N
    Canonical SMILES
    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/[C@H]1C(=CCCC1(C)C)C)\C
    XLogP
    15.187
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    1
    Complexity of molecule
    0.312
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Halobacterium cutirubrum (Ref.331) - Archaea: Euryarchaeota
    Prochlorococcus marinus (Ref.273) - Cyanobacteria
    Prochlorococcus marinus strain CCMP 1986 (Ref.274) - Cyanobacteria
    Prochlorococcus marinus strain CCMP 1375 (Ref.274) - Cyanobacteria
    Prochlorococcus marinus strain CCMP 2773 (Ref.274) - Cyanobacteria
    Bangia alropurpurea (Ref.10) - Red alga: Bangiaceae
    Porphyra perforata (Ref.10) - Red alga: Bangiaceae
    Porphyra perforata (conchocelis)  - Red alga: Bangiaceae
    Scinaia confusa (Ref.10) - Red alga: Nemaliales
    Scinaia latifrons (Ref.10) - Red alga: Nemaliales
    Bonnemaisonia hamifera (Ref.9) - Red alga: Bonnemaisoniales
    Nemalion helminthoides (multifidium)  - 
    Rhodymenia palmata (Ref.9) - Red alga: Palmariales
    Rhodymenia californica (Ref.10) - Red alga: Rhodymeniales
    Fauchea galapagensis (Ref.10) - Red alga: Rhodymeniales
    Antithamnion plumula (Ref.11) - Red alga: Ceramiales
    Ceramium rubrum (Ref.9) - Red alga: Ceramiales
    Grateloupia setchelii (Ref.10) - Red alga: Halymeniales
    Halymenia hollenbergii (Ref.10) - Red alga: Halymeniales
    Prionitis cornea (Ref.10) - Red alga: Halymeniales
    Prionitis lyalii (Ref.10) - Red alga: Halymeniales
    Callophyllis pinnata (Ref.10) - Red alga: Gigartinales
    Gelidium coulteri (Ref.10) - Red alga: Gelidiales
    Gelidium johnstonii (Ref.10) - Red alga: Gelidiales
    Gelidium pusillum (Ref.10) - Red alga: Gelidiales
    Gelidium robustum (Ref.10) - Red alga: Gelidiales
    Pterocladia capillacea (Ref.10) - Red alga: Gelidiales
    Pterocladia lucida (Ref.10) - Red alga: Gelidiales
    Chondracanthus canaliculatus (Ref.10) - Red alga: Gigartinales
    Chondracanthus corymbiferus (Ref.10) - Red alga: Gigartinales
    Chondracanthus exasperatus (Ref.10) - Red alga: Gigartinales
    Chondracanthus spinosus (Ref.10) - Red alga: Gigartinales
    Chondracanthus squarrulosus (Ref.10) - Red alga: Gigartinales
    Iridaea chordata (Ref.10) - Red alga: Gigartinales
    Mazzaella affinis (Ref.10) - Red alga: Gigartinales
    Mazzaella flaccida (Ref.10) - Red alga: Gigartinales
    Mastocarpus papillatus (Ref.10) - Red alga: Gigartinales
    Eucheuma uncinatum (Ref.10) - Red alga: Gigartinales
    Opuntiella californica (Ref.10) - Red alga: Gigartinales
    Plocamium cartilagineum (Ref.10) - Red alga: Plocamiales
    Plocamium violaceae (Ref.10) - Red alga: Plocamiales
    Centroceras clavulatum (Ref.10) - Red alga: Ceramiales
    Neoptilota densa (Ref.10) - Red alga: Ceramiales
    Neoptilota hypnoides (Ref.10) - Red alga: Ceramiales
    Ptilota filicina (Ref.10) - Red alga: Ceramiales
    Acrosorium ciliolatum (Ref.10) - Red alga: Ceramiales
    Asterocolax gardner (Ref.10) - Red alga: Ceramiales
    Cryptopleura farlowiana (Ref.10) - Red alga: Ceramiales
    Cryptopleura lobulifera (Ref.10) - Red alga: Ceramiales
    Phycodrys amplissima (Ref.10) - Red alga: Ceramiales
    Polyneura latissima (Ref.10) - Red alga: Ceramiales
    Bossiella orbignyana (Ref.10) - Red alga: Corallinales
    Corallina officinalis (Ref.10) - Red alga: Corallinales
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
    Ankistrodesmus spp. (Ref.16) - Green alga: Scenedesmaceae
    Pleurastrum paucicellulare (Ref.16) - Green alga: Ulvophyceae
    Oedogonium cardiacum (Ref.16) - Green alga: Chlorophyceae
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Chlorella pyrenoidosa (Ref.21) - Green alga: Trebouxiophyceae
    Chara tomentosa (Ref.25) - Green plants: Charophyceae
    Chara hispida (Ref.25) - Green plants: Charophyceae
    Chara globularis (Ref.25) - Green plants: Charophyceae
    Dunaliella salina (Ref.606) - Green alga: Dunaliellaceae
    Nitella opaca (Ref.25) - Green plants: Charophyceae
    Rhodomonas D3 (Ref.26) - Alga: Cryptomonad
    Chroomonas salina (Ref.26) - Alga: Cryptomonad
    Cryptomonas sp. (Ref.26) - Alga: Cryptomonad
    Cryptomonas ovata (Ref.26) - Alga: Cryptomonad
    Hemiselmis virescens (Ref.26) - Alga: Cryptomonad
    Isochrysis galbana (Ref.31) - Alga: Haptophyte
    Phaeocystis sp. (Ref.31) - Alga: Haptophyte
    Prymnesium parvum (Ref.31) - Alga: Haptophyte
    Coccolithus huxleyi (Ref.32) - Alga: Haptophyte
    Eutreptiella gymnastica (Ref.45) - Alga: Euglenoid
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
    Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte
    Arousa sp. (Ref.46) - Green alga: Prasinophyte
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
    Pycnococcus provasolii (Ref.46) - Green alga: Prasinophyte
    Nephroselmis pyriformis (Ref.46) - Green alga: Prasinophyte
    Pseudoscourfieldia marina (Ref.46) - Green alga: Prasinophyte
    Tetraselmis wettsteinii (Ref.46, Ref.47) - Green alga: Chlorodendraceae
    Tetraselmis sp. (Ref.46, Ref.47) - Green alga: Chlorodendraceae
    Corbicula clams (Ref.221) - 
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Diospyros kaki (Ref.282) - Land plant: kaki persimmon
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika
    Botryococcus braunii Kawaguchi-1 (Ref.231) - Green alga: Trebouxiophyceae
    Extatosoma tiaratum (Ref.308) - Insect: giant prickly stick insect
    Gallus gallus (Ref.309) - Bird: chicken
    Coffea arabica (Ref.323) - Land plant: arabica coffee
    Coffea canephora (Ref.323) - Land plant: robusta coffee
    Agelas schmidtii (Ref.369) - Sea sponge
    Microciona prolifera (Ref.372) - Sea sponge
    Protousnea sp. (Ref.388) - Fungi: lichen
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog
    Elaeis spp. (Ref.431) - Land plant: palm oil
    Galleria mellonella (Ref.558) - Insect: greater wax moth
    Homo sapiens (Ref.407) - Human
    References
  • Ref.331 : Kushwaha, S. C.; Pugh, E. L.; Kramer, J. K. G.; Kates, M., Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1972), 260(3), 492-506., "Isolation and identification of dehydrosqualene and C40 carotenoid pigments in Halobacterium cutirubrum cutirubrum".
  • Ref.273 : Goericke Ralf and Daniel J. Repeta, Limnology and Oceanography Volume 37, Issue 2, pages 425–433, March 1992, "The pigments of Prochlorococcus marinus: The presence of divinylchlorophyll a and b in a marine procaryote".
  • Ref.274 : Shinichi Takaichi, Mari Mochimaru, Hiroko Uchida, Akio Murakami, Euichi Hirose, Takashi Maoka, Tohru Tsuchiya, and Mamoru Mimuro, Plant Cell Physiol. 53(11): 1881–1888 (2012) doi:10.1093/pcp/pcs126, "Opposite Chilarity of a-Carotene in Unusual Cyanobacteria with Unique Chlorophylls, Acaryochloris and Prochlorococcus".
  • Ref.10 : N. Schubert, E. Garcia-Mendoza, and I. Pachecho-Ruiz, J. Phycol. 42, 1208-1216 (2006) "Carotenoid composition of marine red algae".
  • Ref.9 : T. Bjoernland and M. Aguilar-Martinez, Phytochemistry, 1976, Vol.15 pp.291-296, "Carotenoids in red algae".
  • Ref.11 : T. Bjornland, G. Borch, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No 8, pp.1711-1715, 1984. "Configurational studies on red algae carotenoids".
  • Ref.12 : N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13 : PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14 : S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.16 : M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
  • Ref.17 : H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
  • Ref.19 : Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • Ref.21 : B. Stephen Inbaraj, J.T. Chien, B. H. Chen. (2005); "Improved high performance liquid chromatographic method for determination of carotenoids in the microalga Chlorella pyrenoidosa".
  • Ref.25 : M. Schagerl, and Clemens Pichler, Aquatic Botany 67 (2000) 117–129 "Pigment composition of freshwater charophyceae".
  • Ref.606 : K.N. Chidambara Murthy, A. Vanitha, J. Rajesha, M. Mahadeva Swamy, P.R. Sowmya, Gokare A. Ravishankar, Life Sciences 76 (2005) 1381 – 1390, "In vivo antioxidant activity of carotenoids from Dunaliella salina — a green microalga".
  • Ref.26 : F. C. Pennington, F. T. Haxo, G. Borch, and Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 13, No. 3, pp. 215-219, 1985 "Carotenoids of Cryptophyceae".
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.32 : N. Arpin, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1976, Vol. 15, pp. 529-532 "New Fucoxanthin related carotenoids from Coccolithus Huxleyi".
  • Ref.45 : A. Fiksdahl, T. Bjoernland, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No.3, pp. 649-655, 1984, "Algal carotenoids with novel end groups".
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • Ref.47 : E. S. Egeland, W. Eikrem, J. Throndsen, C. Wilhelm, M. Zapata, and S. Liaaen-Jensen, Biochemical systematics and Ecology, Vol. 23, NO. 7/8, pp. 747-755, 1995 "Carotenoids from Further Prasinophytes".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.282 : A. L. Curl, Volume 25, Issue 5, Article first published online: 25 AUG 2006, "The Carotenoids of Jappanese persimmons".
  • Ref.283 : Zoltan Matus, Jozsef Deli, Jozsef Szabolcs, J. Agric. Food Chem., 1991, 39 (11), pp 1907–1914, "Carotenoid composition of yellow pepper during ripening: isolation of .beta.-cryptoxanthin 5,6-epoxide".
  • Ref.231 : Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok, Agrawal, Poonam; Laddha, Kirti; Tiwari, Ashok., "Isolation and HPLC method development of azafrin from Alectra parasitica var. chitrakutensis".
  • Ref.308 : Kayser, Hartmut, Zeitschrift fuer Naturforschung, C:  Journal of Biosciences (1981), 36C(9-10), 755-64., "Carotenoids in the stick insect, Ectatosoma tiaratum.  Isolation of β,ε-carotene-2-ol and β,ε-carotene-2-one".
  • Ref.309 : Matsuno, Takao; Hirono, Toshihiko; Ikuno, Yoshihiro; Maoka, Takashi; Shimizu, Minoru; Komori, Tadaaki, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1986), 84B(4), 477-81., "Isolation of three new carotenoids and proposed metabolic pathways of carotenoids in hen's egg yolk".
  • Ref.323 : Andrew J. Simkin, Marcel Kuntz, Helene Moreau, James McCarthy, Plant Physiology and Biochemistry 48 (2010) pp.434-442, "Carotenoid profiling and the expression of carotenoid biosynthetic genes in developing coffee grain".
  • Ref.369 : Buchecker, Richard; Eugster, Conrad Hans; Litchfield, Carter, Helvetica Chimica Acta, Volume60, Issue8, Pages2780-8, 1977, ISSN:0018-019X, "Carotenoids from marine sponges (Porifera):  isolation and structure of the seven main carotenoids from Agelas schmidtii".
  • Ref.372 : Litchfield, Carter; Liaaen-Jensen, Synnoeve, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1980), 66B(3), 359-65., "Animal carotenoids.  Part 23.  Carotenoids of the marine sponge, Microciona prolifera".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • Ref.421 : Pinky Baruah and Goswami UC., Journal of Research in Biology, pp.114-118, 2012, Vol.2, No.2, "Characterization of carotenoid pigments in amphibian, Rhacophorous bipunctatus".
  • Ref.431 : R. F. Hunter and R. M. Krakenberger, Biochem Jv.40(4); 1946PMC1258385, "Palm-oil carotenoids".
  • Ref.558 : Vitus Oberhausera, Olaf Voolstraa, Annette Bangerta, Johannes von Lintigb, and Klaus Vogt, Proc Natl Acad Sci U S A. 2008 Dec 2;105(48):19000-5. doi: 10.1073/pnas.0807805105. Epub 2008 Nov 19., "NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide.".
  • Ref.407 : Wilhelm Stahl and Helmut Sies, 2012 American Society for Nutrition, "β-Carotene and other carotenoids in protection from sunlight".
  • Ref.408 : Jonathan R Mein, Fuzhi Lian, Xiang-Dong Wang, Nutr Rev. 2008 Dec;66(12):667-83. doi: 10.1111/j.1753-4887.2008.00120.x., PMID: 19019036, "Biological activity of lycopene metabolites: implications for cancer prevention".
  • Ref.467 : Abdulkerim Eroglu and Earl H. Harrison, Journal of Lipid Research Volume 54, 2013, "Carotenoid metabolism in mammals, including man: formation, occurrence, and function of apocarotenoids".
  • Ref.418 : Michiaki Murakoshi, Hoyoku Nishino, Yoshiko Satomi, Junko Takayasu, Teiko Hasegawa, Harukuni Tokuda, Akio Iwashima, Junichi Okuzumi, Hidetoshi Okabe, Hirokazu Kitano, and Ryozo Iwasaki, [CANCER RESEARCH 52, 6583-6587, December 1, 1992], "Potent Preventive Action of a-Carotene against Carcinogenesis: Spontaneous Liver Carcinogenesis and Promoting Stage of Lung and Skin Carcinogenesis in Mice Are Suppressed More Effectively by a-Carotene Than by B-Carotene".
  • Ref.411 : L Le Marchand, J H Hankin, L N Kolonel, G R Beecher, L R Wilkens and L P Zhao, Cancer Epidemiology, Biomarkers & Prevention, vol.2, pp.183-187, May/June 1993, "Intake of specific carotenoids and lung cancer risk.".
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • Ref.491 : Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A., Biol Pharm Bull. 1995 Feb;18(2):227-33., PMID: 7742789, "Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters.".
  • Ref.616 : Takahashi S., Iwasaki-Kino Y., and Terao J., and Mukai K., FOOD COMPOSITION AND ADDITIVES, Journal of AOAC International Vol. 99, no.1, 2016 pp.193-197, "Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method Using a Microplate Reader".
  • Ref.597 : Kazuo MUKAI, Aya OUCHI, Oleoscience, Vol. 13 (2013) No. 8 p. 371-378, "Antioxidant Activity of Foods Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method".
  • Ref.598 : Ouchi, A., Aizawa, K., Iwasaki, Y., Inakuma, T., Terao, J., Nagaoka, S., Mukai, K., 2010. Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. Development of a singlet oxygen absorption capacity (SOAC) assay method. J. Agric. Food Chem. 58, 9967–78. doi:10.1021/jf101947a.
  • Ref.599 : Aizawa, K., Iwasaki, Y., Ouchi, A., Inakuma, T., Nagaoka, S., Terao, J., Mukai, K., 2011. Development of singlet oxygen absorption capacity (SOAC) assay method. 2. Measurements of the SOAC values for carotenoids and food extracts. J. Agric. Food Chem. 59, 3717–29. doi:10.1021/jf104955a .
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • CAS
    7488-99-5, 432-70-2
    Links to other DB
    KEGG COMPOUND: C05433
    KNApSAcK: C00003765
    LipidBank: VCA0009
    MassBank: CA000116, CA000022
    ProCarDB: C1725

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