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Showing Compound alpha-Crocetin diglucosyl ester (FDB018633)

Record Information
Version1.0
Creation date2010-04-08 22:13:50 UTC
Update date2019-11-26 03:16:25 UTC
Primary IDFDB018633
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Crocetin diglucosyl ester
DescriptionIsolated from saffron (Crocus sativus) Dicrocin is a water-soluble crocetin glycoside, a carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. (PMID: 17215084); Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211). alpha-Crocetin diglucosyl ester is found in saffron and herbs and spices.
CAS Number57710-64-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.56ALOGPS
logP0.33ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area232.9 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity168.66 m³·mol⁻¹ChemAxon
Polarizability69.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC32H44O14
IUPAC namebis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
InChI IdentifierInChI=1S/C32H44O14/c1-17(11-7-13-19(3)29(41)45-31-27(39)25(37)23(35)21(15-33)43-31)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(40)26(38)24(36)22(16-34)44-32/h5-14,21-28,31-40H,15-16H2,1-4H3/b6-5+,11-7+,12-8+,17-9-,18-10+,19-13+,20-14-
InChI KeyQBZWPZHDUZGTLS-PVWLSOMFSA-N
Isomeric SMILESC\C(\C=C\C=C(/C)C(=O)OC1OC(CO)C(O)C(O)C1O)=C\C=C\C=C(/C)\C=C\C=C(\C)C(=O)OC1OC(CO)C(O)C(O)C1O
Average Molecular Weight652.6834
Monoisotopic Molecular Weight652.273106116
Classification
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Hexose monosaccharide
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ir3-0405904000-cd1a2e9bf49d83c2019f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-1547901000-586a897db5e40deda2d62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-020r-6897201000-df43c77395d1f1a64fff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1304819000-215867f36c0d7e612afd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022i-4703904000-7bee8d4e713a44c53dcb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9504300000-0527bdbd16e6e80a98d62016-08-03View Spectrum
NMRNot Available
ChemSpider ID17216196
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22833595
Pubchem Substance IDNot Available
ChEBI ID62768
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02353
CRC / DFC (Dictionary of Food Compounds) IDJQK77-A:LLZ65-F
EAFUS IDNot Available
Dr. Duke IDCROCETIN-DI-BETA-GLUCOSIDE|CROCETIN-DI-(BETA-D-GLUCOSYL)-ESTER
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Ochiai T, Shimeno H, Mishima K, Iwasaki K, Fujiwara M, Tanaka H, Shoyama Y, Toda A, Eyanagi R, Soeda S: Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. Biochim Biophys Acta. 2007 Apr;1770(4):578-84. Epub 2006 Dec 5. Pubmed [Structure]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).