Steviol

HCID 452967
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Basic information

CAS
471-80-7
Standard SMILES
C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O)[C@@H]2CC[C@]1(O)C3
InChIKey
QFVOYBUQQBFCRH-VQSWZGCSSA-N
Molecular formula
C20H30O3
Average molar mass
318.4 g/mol
Monoisotopic mass
318.21949482

Overview

Steviol is an ent-kaurane diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group. It has a role as an antineoplastic agent. It is a tertiary allylic alcohol, a monocarboxylic acid, a bridged compound, an ent-kaurane diterpenoid and a tetracyclic diterpenoid. It is a conjugate acid of a steviol(1-).

Names & identifiers

Preferred name
Steviol
IUPAC
(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
English name
Steviol
Molecular formula
C20H30O3
Molecular weight
318.45

Names & synonyms

Steviol471-80-7(-)-SteviolHydroxydehydrostevic acid4741LYX6RTDTXSID50897427(14-alpha)-13-Hydroxykaur-16-en-18-oic acidCHEBI:145024NSC-226902(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acidKaur-16-en-18-oic acid, 13-hydroxy-, (4alpha)-(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo(11.2.1.01,10.04,9)hexadecane-5-carboxylic acid
Show more names
(4R)-13-Hydroxykaur-16-en-18-oic acid2,3,4,4aα,4b,5,6,7,8,8aα,9,10-Dodecahydro-2β-hydroxy-4bβ,8α-dimethyl-12-methylene-1H-2α,10aα-ethanophenanthrene-8β-carboxylic acidSTEVIOL(P)NSC 226902Steviol-RMSteviol StandardSteviol USP/EP/BP
RefChem:185727DTXCID401326770(4R,4aS,6aR,9S,11aR,11bS)-9-Hydroxy-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta(a)naphthalene-4-carboxylic acidMFCD00210558(4R,4aS,6aR,9S,11aR,11bS)-9-hydroxy-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acidKaur-16-en-18-oic acid, 13-hydroxy-, (4.alpha.)-13-Hydroxykaurenoic acid13alpha-hydroxy-5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid

Database identifiers

CAS
471-80-7
PubChem CID
452967
DTXSID
DTXSID50897427
ChEMBL
CHEMBL463996
ChEBI
CHEBI:145024
UNII
4741LYX6RT
Nikkaji
J9.989I

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
23

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]
Collision Cross Section173.38 Ų [M+H]+ [CCS Type: TW]

Physicochemical properties

Melting point
215 ° · 215°
alpha
-94.7 ° · D -94.7°
Boiling point
464.5 · 464.5±45.0 °C(Predicted)
Density
1.17 · 1.17±0.1 g/cm3(Predicted)
storage temp.
2 · Sealed in dry,2-8°C
solubility
10 mg/mL · DMSO: >10mg/mL

Safety & regulation

Safety data

wgk
3
rtecs
NZ8176000
hs_code
29181990
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications

UsesHas been proposed as non-nutritive sweetening agent.

UsesSteviol is an aglycone of the natural sweetener Stevioside (90%, S686730) and is found to be highly mutagenic compared to Stevioside.

Suppliers100 total

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Additional notes · 1 item

DefinitionChEBI: Steviol is an ent-kaurane diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group. It has a role as an antineoplastic agent. It is a tetracyclic diterpenoid, a tertiary allylic alcohol, a monocarboxylic acid, a bridged compound and an ent-kaurane diterpenoid. It is a conjugate acid of a steviol(1-).

Related reactions

4 records
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Compound notes

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