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
Synonyms
SynonymSource
a-Crocetin diglucosyl esterGenerator
Α-crocetin diglucosyl esterGenerator
(all-E)-Crocetin di-b-D-glucopyranosyl estermanual
all-trans-Crocetin di(b-D-glucosyl) estermanual
alpha-Crocetin diglucosyl estermanual
bis(b-D-Glucosyl) crocetinmanual
Crocetin di-(beta-d-glucosyl)-esterbiospider
Crocetin di-(beta-delta-glucosyl)-esterbiospider
Crocetin diglucosyl esterbiospider
Dicrocinmanual
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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 58.89%; H 6.79%; O 34.32%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data475 () (Py)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ir3-0405904000-cd1a2e9bf49d83c2019fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-1547901000-586a897db5e40deda2d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-020r-6897201000-df43c77395d1f1a64fffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1304819000-215867f36c0d7e612afdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022i-4703904000-7bee8d4e713a44c53dcbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9504300000-0527bdbd16e6e80a98d6Spectrum
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
FoodReference
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).