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Record Information
Version1.0
Creation Date2016-05-26 04:17:20 UTC
Update Date2016-11-09 01:20:57 UTC
Accession NumberCHEM033599
Identification
Common Name1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester
ClassSmall Molecule
DescriptionIsolated from Blumea balsamifera, Jasonia species, Salvia fruticosa, carrot, rosemary, sage and lavender oil. Flavouring agent
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(-)-Bornyl acetic acidGenerator
(1S,2R,4S)-(-)-Bornyl acetateHMDB
endo-(1S)-1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl acetateHMDB
FEMA 2159HMDB
L-alpha-Bornyl acetateHMDB
L-Born-2-yl acetateHMDB
L-Bornyl acetateHMDB
Levo-bornyl acetateHMDB
6-[(Acetyloxy)methyl]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (2Z)-5-hydroxy-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoic acidGenerator
1a,3b,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
1a,3b,22R-Trihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
1Α,3β,22R-trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
1Α,3β,22R-trihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
Chemical FormulaC48H76O21
Average Molecular Mass989.104 g/mol
Monoisotopic Mass988.488 g/mol
CAS Registry Number155510-74-0
IUPAC Name6-[(acetyloxy)methyl]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (2Z)-5-hydroxy-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate
Traditional Name6-[(acetyloxy)methyl]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (2Z)-5-hydroxy-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate
SMILESCC(C(O)C\C(C)=C(\C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C1CCC2C3CC=C4CC(CC(O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O
InChI IdentifierInChI=1S/C48H76O21/c1-19(20(2)43(62)69-46-42(39(59)36(56)32(67-46)18-63-22(4)51)68-45-41(61)38(58)35(55)31(17-50)66-45)13-29(52)21(3)26-9-10-27-25-8-7-23-14-24(64-44-40(60)37(57)34(54)30(16-49)65-44)15-33(53)48(23,6)28(25)11-12-47(26,27)5/h7,21,24-42,44-46,49-50,52-61H,8-18H2,1-6H3/b20-19-
InChI KeyCBKQGELSNULPLY-VXPUYCOJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Bornane monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.6 g/LALOGPS
logP-0.98ALOGPS
logP-1.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.85ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area341.51 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity236.94 m³·mol⁻¹ChemAxon
Polarizability104.34 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0101219286-efc6cb3c6a2f97fd9ec6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0102449271-32eada8d90287a67dab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2242809042-dc7709d1e7c23e7803e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9300006067-8fc907d89cd6ade4fa9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9500005052-d5000566a3b71ce118c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9800003100-77d1a54a0c0d94beb0dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0332982137-84d0a1cd184a2afff09aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0923661104-65a3f6fb55f4675022a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0671-6425401096-094bec4b3af6b0fd98d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1004001019-03bd7042a78fe96688c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9200131028-4a36277551092911d24aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9200011041-eced55ad4c9987373bddSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDNot Available
HMDB IDHMDB0040397
FooDB IDFDB020129
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID6207
ChEBI IDNot Available
PubChem Compound ID6448
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM