Steviol

HCID 452967CAS 471-80-7

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Grundinformationen

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
Summenformel: C20H30O3
Durchschnittliche Molmasse: 318,4 g/mol
Monoisotopische Masse: 318,21949482

Überblick

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diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group.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-).

Namen und Bezeichner

Bevorzugter 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
Englischer Name: Steviol
Summenformel: C20H30O3
Molmasse: 318.45

Namen und Synonyme

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

Weitere Namen anzeigen

(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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,8
Polarare Oberfläche (TPSA): 57,5 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 1
Schwere Atome: 23
Formalladung: 0
Komplexität: 583

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]

Collision Cross Section173.38 Å² [M+H]+ [CCS Type: TW]

Physikochemische Eigenschaften

Schmelzpunkt: 215 ° · 215°
Siedepunkt: 464.5 · 464.5±45.0 °C(Predicted)
Dichte: 1.17 · 1.17±0.1 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
Löslichkeit: 10 mg/mL · DMSO: >10mg/mL
Aggregatzustand: powder
pka: 4.65 · 4.65±0.60(Predicted)
Farbe: white to tan
Stabilität: Light Sensitive
InChIKey: QFVOYBUQQBFCRH-ZPNQOMQUSA-N
SMILES: O.C[C@@]12CCC[C@](C)([C@H]1CC[C@]34CC(=C)[C@](O)(CC[C@@H]23)C4)C(O)=O
LogP: 4.035 · 4.035 (est)