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Entry
CA00191                                                            

Classification
Carotenoid Name
γ-Carotene;
gamma-Carotene
IUPAC name beta,psi-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Provitamin A.
  • Pinkish-brown color (Ref.430).
  • Yellow food coloring (Ref.468).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
  • Constitutional isomer: CA00043, CA00045, CA00298, CA00305, CA00309, CA00587, CA01191, CA00677, CA00680, CA00681, CA00720
  • Cis/trans isomer: CA00192
  • InChI
    InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
    InChIKey
    HRQKOYFGHJYEFS-BXOLYSJBSA-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=C(/CCC=C(C)C)\C)\C
    XLogP
    14.660
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.062
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Chlorobium tepidum (Ref.355) - Green sulfur bacteria
    Oscillatoria princeps (Ref.1) - Cyanobacteria
    Chara tomentosa (Ref.25) - Green plants: Charophyceae
    Chara contraria (Ref.25) - Green plants: Charophyceae
    Chara hispida (Ref.25) - Green plants: Charophyceae
    Chara polyacantha (Ref.25) - Green plants: Charophyceae
    Chara rudis (Ref.25) - Green plants: Charophyceae
    Chara globularis (Ref.25) - Green plants: Charophyceae
    Chara aspera (Ref.25) - Green plants: Charophyceae
    Nitella opaca (Ref.25) - Green plants: Charophyceae
    Euglena gracilis (Ref.37) - Alga: Euglenoid
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Nephroselmis rotunda (Ref.46, Ref.47) - Green alga: Prasinophyte
    Coccinella septempunctata (Ref.116) - Insect: seven-spotted ladybird
    Macrosiphum liriodendri (Ref.118) - Insect: aphid
    Rhodobacter sphaeroides (Ref.208) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit
    Citrullus vulgaris (Ref.484) - Land plant: watermelon
    Rhodotorula minuta (Ref.506) - Fungi: red yeast
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Elaeis spp. (Ref.431) - Land plant: palm oil
    References
  • Ref.355 : Takaichi, Shinichi; Wang, Zheng-Yu; Umetsu, Mitsuo; Nozawa, Tsunenori; Shimada, Keizo; Madigan, Michael T., Archives of Microbiology (1997), 168(4), 270-276., "New carotenoids from the thermophilic green sulfur bacterium Chlorobium tepidum: 1',2'-dihydro-γ-carotene, 1',2'-dihydrochlorobactene, and OH-chlorobactene glucoside ester, and the carotenoid composition of different strains".
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.25 : M. Schagerl, and Clemens Pichler, Aquatic Botany 67 (2000) 117–129 "Pigment composition of freshwater charophyceae".
  • Ref.37 : N. I. Krinsky, and T. H. Goldsmith, Archives of Biochemistry and Biophysics 91, 271-279 (1960), "The Carotenoids of the Flagellated Alga, Euglena gracilis".
  • Ref.42 : B.Czeczuga, Comp. Biochem. Physiol., 1974, Vol. 48B, pp. 349-354, "Carotenoids in Euglena rubida mainx".
  • 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.116 : Britton, George; Lockley, William J. S.; Harriman, Garry A.; Goodwin, Trevor W., Nature (London, United Kingdom) (1977), 266(5597), 49-50., "Pigmentation of the ladybird beetle Coccinella septempunctata by carotenoids not of plant origin".
  • Ref.118 : Andrewes, A. G.; Kjoesen, H.; Liaaen-Jensen, S.; Weisgraber, K. H.; Lousberg, R. J. J. C.; Weiss, U., Acta Chemica Scandinavica (1947-1973) (1971), 25(10), 3878-80., "Animal carotenoids. 7. Carotenes of two color variants of the aphid Macrosiphum liriodendri. Identification of natural γ,​γ-​carotene".
  • Ref.208 : M Albrecht, A Ruther, G Sandmann, J. Bacteriol. December 1997 vol. 179 no. 23 7462-7467, "Purification and biochemical characterization of a hydroxyneurosporene desaturase involved in the biosynthetic pathway of the carotenoid spheroidene in Rhodobacter sphaeroides.".
  • Ref.129 : da Silva, Sandra Regina; Mercadante, Adriana Z., Ciencia e Tecnologia de Alimentos (Campinas, Brazil) (2002), 22(3), 254-258., "Carotenoid composition of fresh yellow passion fruit (Passiflora edulis flavicarpa)".
  • Ref.484 : Wen’en Zhao, Pin Lv, Huihui Gu, Agricultural Sciences Vol.4, No.7A, 13-20 (2013), http://dx.doi.org/10.4236/as.2013.47A003, "Studies on carotenoids in watermelon flesh".
  • Ref.506 : K. Shivalkar Yada and R. Prabha, Indian Journal of Science and Technology, Vol 7(12), 1973–1977, December 2014, ISSN (Print) : 0974-6846 , ISSN (Online) : 0974-5645, "Extraction of Pigments from Rhodotorula Species of Dairy Environment".
  • Ref.430 : T. W. GOODWIN, Biochem J. 1954 Sep;58(1):90-4., "Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.".
  • Ref.431 : R. F. Hunter and R. M. Krakenberger, Biochem Jv.40(4); 1946PMC1258385, "Palm-oil carotenoids".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    472-93-5
    Links to other DB
    KEGG COMPOUND: C05435
    KNApSAcK: C00000926
    LipidBank: VCA1007
    MassBank: CA000163
    ProCarDB: C1802

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