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Record Information
Version2.0
Created at2022-04-28 09:56:53 UTC
Updated at2022-04-28 09:56:53 UTC
NP-MRD IDNP0065750
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-keto-gamma-Carotene
Description4-Keto-gamma-carotene/ keto-gamma-carotene belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, 4-keto-gamma-carotene/ keto-gamma-carotene is considered to be an isoprenoid. 4-keto-gamma-Carotene is found in Arthrobacter sp., Deinococcus radiodurans, Gordonia terrae, Mycobacterium phlei, Mycobacterium smegmatis, Myxococcus fulvus and Stigmatella aurantiaca. 4-keto-gamma-Carotene was first documented in 2006 (PMID: 16928467). Based on a literature review a small amount of articles have been published on 4-keto-gamma-carotene/ keto-gamma-carotene (PMID: 27866612) (PMID: 22790171) (PMID: 22056433) (PMID: 16133327).
Structure
Thumb
Synonyms
ValueSource
4-Keto-g-carotene/ keto-g-caroteneGenerator
4-Keto-γ-carotene/ keto-γ-caroteneGenerator
Chemical FormulaC40H54O
Average Mass550.8710 Da
Monoisotopic Mass550.41747 Da
IUPAC Name3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
Traditional Name3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
InChI Identifier
InChI=1S/C40H54O/c1-31(2)17-13-20-34(5)23-15-25-35(6)24-14-21-32(3)18-11-12-19-33(4)22-16-26-36(7)27-28-38-37(8)39(41)29-30-40(38,9)10/h11-12,14-19,21-28H,13,20,29-30H2,1-10H3/b12-11+,21-14+,22-16+,25-15+,28-27+,32-18+,33-19+,34-23+,35-24+,36-26+
InChI KeyBRKQDNOGSHYATK-HNNISBQLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.04ALOGPS
logP10.86ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)19.89ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity195.4 m³·mol⁻¹ChemAxon
Polarizability73.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00022972
Chemspider ID17220949
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061281
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sowani H, Mohite P, Damale S, Kulkarni M, Zinjarde S: Carotenoid stabilized gold and silver nanoparticles derived from the Actinomycete Gordonia amicalis HS-11 as effective free radical scavengers. Enzyme Microb Technol. 2016 Dec;95:164-173. doi: 10.1016/j.enzmictec.2016.09.016. Epub 2016 Sep 28. [PubMed:27866612 ]
  2. Maoka T, Etoh T, Osawa A, Shindo K: Characterization and singlet oxygen quenching activity of (3R)-3-hydroxy-4-ketotorulene and (3R)-3-hydroxy-4-keto-gamma-carotene isolated from the yeast Xanthophyllomyces dendrorhrous. J Oleo Sci. 2012;61(7):401-6. doi: 10.5650/jos.61.401. [PubMed:22790171 ]
  3. Osawa A, Kasahara A, Mastuoka S, Gassel S, Sandmann G, Shindo K: Isolation of a novel carotenoid, OH-chlorobactene glucoside hexadecanoate, and related rare carotenoids from Rhodococcus sp. CIP and their antioxidative activities. Biosci Biotechnol Biochem. 2011;75(11):2142-7. doi: 10.1271/bbb.110441. Epub 2011 Nov 7. [PubMed:22056433 ]
  4. Sandmann G, Zhu C, Krubasik P, Fraser PD: The biotechnological potential of the al-2 gene from Neurospora [correction of Neurospra] crassa for the production of monocyclic keto hydroxy carotenoids. Biochim Biophys Acta. 2006 Sep;1761(9):1085-92. doi: 10.1016/j.bbalip.2006.06.002. Epub 2006 Jul 1. [PubMed:16928467 ]
  5. Tao L, Wagner LW, Rouviere PE, Cheng Q: Metabolic engineering for synthesis of aryl carotenoids in Rhodococcus. Appl Microbiol Biotechnol. 2006 Mar;70(2):222-8. doi: 10.1007/s00253-005-0064-0. Epub 2005 Aug 17. [PubMed:16133327 ]