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Showing Compound 4-Acetyl-2-prenylphenol glucoside (FDB017580)

Record Information
Version1.0
Creation date2010-04-08 22:13:10 UTC
Update date2019-11-26 03:14:57 UTC
Primary IDFDB017580
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Acetyl-2-prenylphenol glucoside
Description4-Acetyl-2-prenylphenol glucoside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 4-Acetyl-2-prenylphenol glucoside has been detected, but not quantified in, several different foods, such as herbs and spices, green tea, black tea, red tea, and teas (Camellia sinensis). This could make 4-acetyl-2-prenylphenol glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Acetyl-2-prenylphenol glucoside.
CAS Number26932-05-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4-Acetyl-2-prenylphenol glucosidemanual
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone O-b-D-glucopyranosidemanual
Predicted Properties
PropertyValueSource
Water Solubility1.5 g/LALOGPS
logP0.47ALOGPS
logP0.69ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.83 m³·mol⁻¹ChemAxon
Polarizability38.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O7
IUPAC name1-[3-(3-methylbut-2-en-1-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl]ethan-1-one
InChI IdentifierInChI=1S/C19H26O7/c1-10(2)4-5-13-8-12(11(3)21)6-7-14(13)25-19-18(24)17(23)16(22)15(9-20)26-19/h4,6-8,15-20,22-24H,5,9H2,1-3H3
InChI KeyGVWZZKUSNVNWGC-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C(OC2OC(CO)C(O)C(O)C2O)C=CC(=C1)C(C)=O
Average Molecular Weight366.4055
Monoisotopic Molecular Weight366.167853186
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • O-glycosyl compound
  • Acetophenone
  • Phenylketone
  • Phenoxy compound
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Ketone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.28%; H 7.15%; O 30.57%DFC
Melting PointMp 160°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -45 (c, 0.1 in MeOH)DFC
Spectroscopic UV Data226 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Acetyl-2-prenylphenol glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abj-9347000000-41263e80430cfd20f2dbSpectrum
Predicted GC-MS4-Acetyl-2-prenylphenol glucoside, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7c-1121129000-50ffd2da7d5dcf7fa203Spectrum
Predicted GC-MS4-Acetyl-2-prenylphenol glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aos-0569000000-b8b4ce7248d38574a8b72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2971000000-b26dac2c8d1a4196f58e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n1-4920000000-44aa45bcb39303be01082015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-1359000000-2e92f6115ed3a820bf172015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1492000000-b13de36406cced6603c52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-4960000000-421a2504d4a43331a2832015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0159000000-73ca2d79da1e4c31b1162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2259000000-89214089bdaa214397a82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-5941000000-d5b8b8eef8da6c95d5652021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0319000000-2461dce0e044d9f779162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0938000000-c9e58c5b2a0a5bf7ff032021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-2390000000-d34f6f9663b6c4ba71e32021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38282
CRC / DFC (Dictionary of Food Compounds) IDCND38-M:KYH73-W
EAFUS IDNot Available
Dr. Duke IDNot Available
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 ReferenceNot Available
Content Reference