SAFFRON (CROCUS SATIVUS L.) (CHEM007438)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:25:40 UTC
Update Date2016-11-09 01:09:55 UTC
Accession NumberCHEM007438
Identification
Common NameSAFFRON (CROCUS SATIVUS L.)
ClassSmall Molecule
DescriptionA diester that is crocetin in which both of the carboxy groups have been converted to their gentiobiosyl esters. It is one of the water-soluble yellow-red pigments of saffron and is used as a spice for flavouring and colouring food. Note that in India, the term 'Crocin' is also used by GlaxoSmithKline as a brand-name for paracetamol.
Contaminant Sources
  • EAFUS Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-CrocinChEBI
Bis(beta-D-gentiobiosyl) crocetinChEBI
C.I. 75100ChEBI
Crocetin di-beta-D-gentiobiose esterChEBI
Crocetin di-gentiobiose esterChEBI
Crocetin digentiobiosideChEBI
CrocineChEBI
Natural red 1ChEBI
Natural yellow 19ChEBI
Natural yellow 6ChEBI
SaffronChEBI
trans-Crocetin bis(beta-D-gentiobiosyl) esterChEBI
a-CrocinGenerator
Α-crocinGenerator
Bis(b-D-gentiobiosyl) crocetinGenerator
Bis(β-D-gentiobiosyl) crocetinGenerator
Crocetin di-b-D-gentiobiose esterGenerator
Crocetin di-β-D-gentiobiose esterGenerator
trans-Crocetin bis(b-D-gentiobiosyl) esterGenerator
trans-Crocetin bis(β-D-gentiobiosyl) esterGenerator
all-trans-Crocetin di-beta-D-gentiobiosyl esterHMDB
all-trans-Crocetin di-beta-delta-gentiobiosyl esterHMDB
Crocetin bis(gentiobiosyl) esterHMDB
Crocetin digentiobiose esterHMDB
Crocin 1HMDB
Gardenia yellowHMDB
Saffron (JP15)HMDB
CrocinMeSH
Chemical FormulaC44H64O24
Average Molecular Mass976.972 g/mol
Monoisotopic Mass976.379 g/mol
CAS Registry Number977051-90-3
IUPAC Namebis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
Traditional Namesaffron
SMILESC\C(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
InChI KeySEBIKDIMAPSUBY-RTJKDTQDSA-N
Chemical Taxonomy
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
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP-0.02ALOGPS
logP-3.2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.67ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area391.2 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity233.49 m³·mol⁻¹ChemAxon
Polarizability100.07 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-0000008009-3b75a0bb1954441908e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0002009000-9e622eb534e813be910cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0059-1259001000-27e1be6013a6ff14a567Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0570-0107109005-8d4ac227319c8db4f8a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0316529102-33fcee1955a03eb2acbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mr-1948544002-585ea2a4ab28ee86f4acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1514037019-77be269ba2dd85c94f6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c29-3914005115-42287fc2024b10a75c14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uml-8933015221-e452e968e696d68b4e6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0101229114-188a76b2b8dade56be41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ce9-0384029001-234bd0906e1d9e993e0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0491033013-b4cd69b33ee6311f8a36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pk9-0018019003-dec192fc122debfcf133Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-4200019082-19b8afa05b75bf20b85bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2000009001-de243920ac2be1b58304Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11874
HMDB IDHMDB0002398
FooDB IDFDB014549
Phenol Explorer IDNot Available
KNApSAcK IDC00003769
BiGG IDNot Available
BioCyc IDCPD-8666
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCrocin
Chemspider ID4444645
ChEBI ID79068
PubChem Compound ID5281233
Kegg Compound IDC08589
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14514073
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17704979
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21398065
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24132704
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24275090
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24401376
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24659065
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24697694
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24839356
10. 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.
11. Carmona M, Zalacain A, Sanchez AM, Novella JL, Alonso GL: Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS. J Agric Food Chem. 2006 Feb 8;54(3):973-9.