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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-10-13 04:39:09 UTC
HMDB IDHMDB0002376
Secondary Accession Numbers
  • HMDB02376
Metabolite Identification
Common NameTricrocin
DescriptionTricrocin 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 ).
Structure
Data?1582752247
Synonyms
ValueSource
Crocetin-(beta-D-gentiobiosyl)-(beta-D-glucosyl)-esterHMDB
Crocetin-(beta-delta-gentiobiosyl)-(beta-delta-glucosyl)-esterHMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (6S)-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-heptaenedioic acidHMDB
Chemical FormulaC38H54O19
Average Molecular Weight814.824
Monoisotopic Molecular Weight814.325929546
IUPAC Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (6S)-3,4,5-trihydroxy-6-({[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 Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (6S)-3,4,5-trihydroxy-6-({[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
CAS Registry Number55750-84-0
SMILES
C\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)OC1O[C@@H](COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C38H54O19/c1-18(11-7-13-20(3)34(50)56-37-32(48)29(45)26(42)23(16-40)54-37)9-5-6-10-19(2)12-8-14-21(4)35(51)57-38-33(49)30(46)27(43)24(55-38)17-52-36-31(47)28(44)25(41)22(15-39)53-36/h5-14,22-33,36-49H,15-17H2,1-4H3/b6-5+,11-7+,12-8+,18-9+,19-10+,20-13+,21-14+/t22-,23?,24+,25-,26?,27?,28+,29?,30?,31-,32?,33?,36-,37?,38?/m1/s1
InChI KeyCZSBHMFVVLYIQQ-AUXQCMSZSA-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility346.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP10(0.75) g/LALOGPS
logP10(-1.4) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area312.05 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity201.07 m³·mol⁻¹ChemAxon
Polarizability84.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TricrocinC\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)OC1O[C@@H](COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O7263.1Standard polar33892256
TricrocinC\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)OC1O[C@@H](COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O5796.7Standard non polar33892256
TricrocinC\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)OC1O[C@@H](COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O6417.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricrocin GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 10V, Positive-QTOFsplash10-03ms-0309606310-ac73a7bee1b2572f86da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 20V, Positive-QTOFsplash10-03ki-0347905100-1ab4b204006078e4e6152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 40V, Positive-QTOFsplash10-020s-1879302300-553c99da3ff6429ef5212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 10V, Negative-QTOFsplash10-0h3b-0428839750-a0b5c17e640b882756f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 20V, Negative-QTOFsplash10-01vk-4615505900-f09bfc9cb493c5612f682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 40V, Negative-QTOFsplash10-0473-6924311400-d6d910503c1c4406a1482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 10V, Negative-QTOFsplash10-03di-0809007160-a2101d4fdedb8623eec32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 20V, Negative-QTOFsplash10-0pb9-2200019510-c7f88bae06d636ecf5b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 40V, Negative-QTOFsplash10-0a4i-2011029000-6208f8917829fd03eb1b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 10V, Positive-QTOFsplash10-00kk-0615319230-ac2757ba82ad761625e52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 20V, Positive-QTOFsplash10-03y0-0887119010-42bea49d9aa5724b60cf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricrocin 40V, Positive-QTOFsplash10-001i-3950013000-343d647b9e05dff1e3e92021-09-25Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018634
KNApSAcK IDC00045803
Chemspider ID17216203
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833598
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1874421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]