Record Information
Version1.0
Creation date2010-04-08 22:10:46 UTC
Update date2018-05-29 01:05:48 UTC
Primary IDFDB013538
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameStevioside
DescriptionConstituent of Stevia rebaudiana (stevia). Sweetening agent which is 300 times sweeter than sucrose. Stevia rebaudiana is extensively cultivated in Japan, and Stevioside is a permitted sweetener in that country Rebaudioside B, D, and E may also be present in minute quantities; however, it is suspected that rebaudioside B is a byproduct of the isolation technique. The two majority compounds stevioside and rebaudioside, primarily responsible for the sweet taste of stevia leaves, were first isolated by two French chemists in 1931.
CAS Number57817-89-7
Structure
Thumb
Synonyms
SynonymSource
Diterpene glycosideHMDB
Eupatorin?HMDB
RebaudinHMDB
Stevin?HMDB
SteviosinHMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acidGenerator
SteviosideMeSH
Steviol glycosideMeSH
Predicted Properties
PropertyValueSource
Water Solubility4.51 g/LALOGPS
logP-1.2ALOGPS
logP-2.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area294.98 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity186.15 m³·mol⁻¹ChemAxon
Polarizability83.95 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC38H60O18
IUPAC name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate
InChI IdentifierInChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3
InChI KeyUEDUENGHJMELGK-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C1CCC13CC(=C)C(C1)(CCC23)OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O
Average Molecular Weight804.8722
Monoisotopic Molecular Weight804.377965116
Classification
Description Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentSteviol glycosides
Alternative Parents
Substituents
  • Steviol glycoside
  • Diterpenoid
  • Kaurane diterpenoid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.71%; H 7.51%; O 35.78%DFC
Melting PointMp 238-239°DFC
Boiling PointNot Available
Experimental Water Solubility1.25 mg/mLMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -39.3 (c, 5.7 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-0103809210-618c8917bf91bf14e0daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-040r-0104904000-6810fe906f79bdcb23c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02w9-0415902100-c4cc22c8df7fa9e745e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fic-1402569430-00c6ad06eb887c4431b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1911715300-ccd331e4189584049205Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4901410000-d567568eafd4a9c77616Spectrum
NMRNot Available
ChemSpider ID477115
ChEMBL IDNot Available
KEGG Compound IDC09189
Pubchem Compound ID548198
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34945
CRC / DFC (Dictionary of Food Compounds) IDJFC43-A:JFC44-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003485
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDStevioside
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