Record Information
Version1.0
Creation date2010-04-08 22:09:17 UTC
Update date2018-05-28 22:49:17 UTC
Primary IDFDB010773
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzyl isothiocyanate rhamnoside
Description4-Hydroxybenzyl isothiocyanate rhamnoside 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-Hydroxybenzyl isothiocyanate rhamnoside is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxybenzyl isothiocyanate rhamnoside has been detected, but not quantified in, herbs and spices. This could make 4-hydroxybenzyl isothiocyanate rhamnoside a potential biomarker for the consumption of these foods.
CAS Number73255-40-0
Structure
Thumb
Synonyms
SynonymSource
4-Hydroxybenzyl isothiocyanic acid rhamnosideGenerator
4-Hydroxybenzyl isothiocyanate O-a-L-rhamnopyranosidemanual
4-Hydroxybenzyl isothiocyanate rhamnosidemanual
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.42ALOGPS
logP1.27ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area91.51 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.52 m³·mol⁻¹ChemAxon
Polarizability31.9 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H17NO5S
IUPAC name2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol
InChI IdentifierInChI=1S/C14H17NO5S/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-15-7-21/h2-5,8,11-14,16-18H,6H2,1H3
InChI KeyQAZIHHJTZPNRCM-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O
Average Molecular Weight311.353
Monoisotopic Molecular Weight311.082743349
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.01%; H 5.50%; N 4.50%; O 25.69%; S 10.30%DFC
Melting PointMp 74°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[base] lmax 221 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-9640000000-6207d6b31a0ee31657b8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3942370000-1fe633044ead93f36592JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0943000000-603d5b6571df56befc88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0910000000-13def0973881f675eeedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-d8a303bca8fe9df2b797JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-6849000000-f12dbc47dda4fff75160JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4910000000-d94bb095929fc3374520JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-44b7fb511350b287577bJSpectraViewer
ChemSpider ID11590012
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14865502
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32801
CRC / DFC (Dictionary of Food Compounds) IDFBT52-P:FON45-Y
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