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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:52 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002398
Secondary Accession Numbers
  • HMDB02398
Metabolite Identification
Common NameCrocin
DescriptionCrocin is a water-soluble 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. Crocin suppresses tumor necrosis factor (TNF)alpha-induced apoptosis of pheochromocytoma (PC12) cells by modulating mRNA expressions of Bcl-2 family proteins, which trigger downstream signals culminating in caspase-3 activation followed by cell death. Depriving cultured PC12 cells of serum/glucose causes a rapid increase in cellular ceramide levels, followed by an increase in the risk of cell death. The accumulation of ceramide was found to depend on the activation of neutral sphingomyelinase (nSMase). Crocin prevented the activation of nSMase by enhancing the transcription of gamma-glutamylcysteinyl synthase, which contributes to a stable glutathione supply that blocks the activity of nSMase. (PMID: 17215084 ). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211 ).
Structure
Data?1582752248
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 Weight976.972
Monoisotopic Molecular Weight976.378752941
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
CAS Registry Number42553-65-1
SMILES
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)=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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling Point1169.04 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3688 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-4.742 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+291.71730932474
DeepCCS[M-H]-289.99430932474
DeepCCS[M-2H]-324.02630932474
DeepCCS[M+Na]+297.95130932474
AllCCS[M+H]+294.232859911
AllCCS[M+H-H2O]+294.632859911
AllCCS[M+NH4]+293.832859911
AllCCS[M+Na]+293.732859911
AllCCS[M-H]-308.632859911
AllCCS[M+Na-2H]-315.132859911
AllCCS[M+HCOO]-322.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Crocin 10V, Negative-QTOFsplash10-0fb9-0000008009-3b75a0bb1954441908e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Crocin 20V, Negative-QTOFsplash10-0udi-0002009000-9e622eb534e813be910c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Crocin 40V, Negative-QTOFsplash10-0059-1259001000-27e1be6013a6ff14a5672021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 10V, Positive-QTOFsplash10-0570-0107109005-8d4ac227319c8db4f8a82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 20V, Positive-QTOFsplash10-01p9-0316529102-33fcee1955a03eb2acbe2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 40V, Positive-QTOFsplash10-03mr-1948544002-585ea2a4ab28ee86f4ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 10V, Negative-QTOFsplash10-004i-1514037019-77be269ba2dd85c94f6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 20V, Negative-QTOFsplash10-0c29-3914005115-42287fc2024b10a75c142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 40V, Negative-QTOFsplash10-0uml-8933015221-e452e968e696d68b4e6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 10V, Positive-QTOFsplash10-0a70-0101229114-188a76b2b8dade56be412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 20V, Positive-QTOFsplash10-0ce9-0384029001-234bd0906e1d9e993e0b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 40V, Positive-QTOFsplash10-001i-0491033013-b4cd69b33ee6311f8a362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 10V, Negative-QTOFsplash10-0pk9-0018019003-dec192fc122debfcf1332021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 20V, Negative-QTOFsplash10-0bt9-4200019082-19b8afa05b75bf20b85b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Crocin 40V, Negative-QTOFsplash10-0a4i-2000009001-de243920ac2be1b583042021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11874
Phenol Explorer Compound IDNot Available
FooDB IDFDB014549
KNApSAcK IDC00003769
Chemspider ID4444645
KEGG Compound IDC08589
BioCyc IDCPD-8666
BiGG IDNot Available
Wikipedia LinkCrocin
METLIN IDNot Available
PubChem Compound5281233
PDB IDNot Available
ChEBI ID79068
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1281461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  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:17215084 ]
  2. 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. [PubMed:16448211 ]