Record Information
Version1.0
Creation date2010-04-08 22:12:07 UTC
Update date2019-11-26 03:12:25 UTC
Primary IDFDB015899
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGrandiflorolic acid
Descriptiondelta-Carotene-1,2-epoxide 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. delta-Carotene-1,2-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number22338-69-8
Structure
Thumb
Synonyms
SynonymSource
Δ-carotene-1,2-epoxideGenerator
1',2'-Epoxy-1',2'-dihydro-e,y-caroteneHMDB
1',2'-Epoxy-1',2'-dihydro-epsilon,psi-caroteneHMDB
D-Carotene-1,2-epoxideHMDB
Gradifloric acidHMDB
Grandifloric acidHMDB
15-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
GrandiflorolateGenerator
Grandiflorolic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.29ALOGPS
logP3.73ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
pKa (Strongest Basic)-0.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.73 m³·mol⁻¹ChemAxon
Polarizability36.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O3
IUPAC name15-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
InChI IdentifierInChI=1S/C20H30O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)
InChI KeyGVGJRXSJJHLPGZ-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
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
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.43%; H 9.49%; O 15.07%DFC
Melting PointMp 216-218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGrandiflorolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0293000000-6d81233578562a5d26aaSpectrum
Predicted GC-MSGrandiflorolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0092-7057900000-207d915177a4f066ae38Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0049000000-4b652304c7d71bce7fdaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0295000000-15eccd134beb9a35a29cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-6891000000-4421f81b0af8e634e443Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0069000000-718245f7e353ddb6470bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0601-0093000000-1abaaf43e0d70f316624Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-0091000000-e4fe010c6ed57c8ce4f1Spectrum
NMRNot Available
ChemSpider ID383411
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID433554
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36930
CRC / DFC (Dictionary of Food Compounds) IDJGR61-I:KKJ13-U
EAFUS IDNot Available
Dr. Duke IDGRANDIFLORIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelopathicDUKE
anti feedantDUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
larvicideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
utero tonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).