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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2020-02-26 21:23:54 UTC
HMDB IDHMDB0002181
Secondary Accession Numbers
  • HMDB0011186
  • HMDB02181
  • HMDB11186
Metabolite Identification
Common NamePhytoene
DescriptionPhytoene, also known as 7,7',8,8',11,11',12,12'-octahydrocarotene, is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048 , 15003396 ).
Structure
Data?1582752234
Synonyms
ValueSource
(6E,10E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaeneChEBI
7,7',8,8',11,11',12,12'-Octahydro-psi,psi-caroteneChEBI
(all-e)-PhytoeneHMDB
all-trans-7,7',8,8',11,11',12,12'-Octahydro-lycopeneHMDB
all-trans-PhytoeneHMDB
trans-PhytoeneHMDB
(all-e) PhytoeneHMDB
7,7',8,8',11,11',12,12'-Octahydro-ψ,ψ-caroteneHMDB
7,7’,8,8’,11,11’,12,12’-octahydro-ψ,ψ-caroteneHMDB
Chemical FormulaC40H64
Average Molecular Weight544.9362
Monoisotopic Molecular Weight544.500802048
IUPAC Name(6E,10E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
Traditional Namephytoene
CAS Registry Number540-04-5
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H64/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,19-22,27-30H,13-18,23-26,31-32H2,1-10H3/b12-11+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
InChI KeyYVLPJIGOMTXXLP-KEKOKYSKSA-N
Chemical Taxonomy
Description 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
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP9.6ALOGPS
logP13.38ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity193.34 m³·mol⁻¹ChemAxon
Polarizability74.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available239.5831661259
DarkChem[M-H]-PredictedNot Available228.74631661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0570-6737950000-7711f2e47eaad6db7dec2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0221190000-3244d5283223f5646dea2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a73-2984620000-0979dace9bacc0f9a33c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-3777900000-f7a566e5a1a7d0e859652017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-5470ec221f64751881192017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000090000-0fab68faee101ed9388b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1964680000-912b2d47f235939dc5c72017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.08 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.23 +/- 0.16 uMAdult (>18 years old)BothNormal details
Breast MilkDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030667
KNApSAcK IDC00000905
Chemspider ID4444344
KEGG Compound IDC05413
BioCyc IDPHYTOENE
BiGG IDNot Available
Wikipedia LinkPhytoene
METLIN IDNot Available
PubChem Compound5280784
PDB IDNot Available
ChEBI ID8191
Food Biomarker OntologyNot Available
VMH IDPHYTN
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
  2. Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]