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Showing Compound Steviol (FDB015642)

Record Information
Version1.0
Creation date2010-04-08 22:11:58 UTC
Update date2019-11-26 03:11:58 UTC
Primary IDFDB015642
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSteviol
DescriptionIsolated from Cucurbita maxima 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. Steviol is found in fruits and japanese pumpkin.
CAS Number471-80-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-SteviolHMDB
13-Hydroxy-kaur-16-en-18-Oic acidHMDB
Hydroxydehydrostevic acidHMDB
13-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
Steviol, (+,-)-isomerMeSH
Steviol, 3H-labeledMeSH
SteviolMeSH
Kaur-16-en-18-oic acid, 13-hydroxy-biospider
Kaur-16-en-18-oic acid, 13-hydroxy-, (4α)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.18ALOGPS
logP3.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.89 m³·mol⁻¹ChemAxon
Polarizability36.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O3
IUPAC name13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
InChI IdentifierInChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)
InChI KeyQFVOYBUQQBFCRH-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C1CCC13CC(=C)C(O)(C1)CCC23)C(O)=O
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.43%; H 9.49%; O 15.07%DFC
Melting PointMp 215°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -94.7 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSteviol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udl-0192000000-de1090a4ec1533cb323cSpectrum
Predicted GC-MSSteviol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0092-7036900000-a2aed9f4962f4d61b3bfSpectrum
Predicted GC-MSSteviol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0049000000-5ae9a49dfa780b709aaa2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0295000000-de545938e500f87f71372015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvl-3960000000-187f3853f760d905241c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0069000000-efddc327a3da1c119a4d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0601-0093000000-f5154216ed6952d774ec2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1091000000-7c1aee023932b02e7beb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-062ad2a35e11d303cf232021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-062ad2a35e11d303cf232021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2029000000-20b48f0aaf7fb62a56c32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0095000000-18d0bd8a33d68ee36ccb2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05xr-0092000000-6cbbad8923153dd4cebd2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-4961000000-5bea034cb1da2fd59ca82021-09-25View Spectrum
NMRNot Available
ChemSpider ID277096
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID313280
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36706
CRC / DFC (Dictionary of Food Compounds) IDJFC43-A:KFK00-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00034695
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSteviol
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