18Alpha-Glycyrrhetinic Acid
Basic information
- CAS
1449-05-4- Standard SMILES
CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12- InChIKey
MPDGHEJMBKOTSU-PMTKVOBESA-N- Molecular formula
- C30H46O4
- Average molar mass
- 470.7 g/mol
- Monoisotopic mass
- 470.33960994
Overview
18alpha-Glycyrrhetinic acid has been reported in Glycyrrhiza uralensis and Glycyrrhiza glabra with data available.
Names & identifiers
- Preferred name
- 18Alpha-Glycyrrhetinic Acid
- IUPAC
- (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
- English name
- 18alpha-Glycyrrhetinic acid
- Molecular formula
- C30H46O4
- Molecular weight
- 470.68
Names & synonyms
18alpha-Glycyrrhetinic acid1449-05-4(18alpha)-3beta-Hydroxy-11-oxoolean-12-en-30-oic acid(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acidDTXSID2087240818alpha-GA18beta-GARefChem:79413DTXCID30820056215-907-9beta-Glycyrrhetinic acid18a-glycyrrhetinic acid
Show more names
Nsc 35350TriterpeneCcris 3963Brn 2956366Einecs 215-907-918α-GlycyrrhetinicEnoxolone impurity A18α-Glycyrrhetic acid
18-Isoglycyrrhetinic acid(3beta,18alpha,20beta)-3-Hydroxy-11-oxoolean-12-en-29-oic acidEnoxolone EP Impurity AMFCD0006489718a-Glycyrrhetic acid18-alpha-Glycyrrhetinic acid(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acidOlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3beta,18alpha,20beta)-
Database identifiers
- CAS
1449-05-4- PubChem CID
- 73398
- DTXSID
DTXSID20872408- ChEMBL
CHEMBL454067- UNII
- X6NYL2CP2E
- EC Number
- 215-907-9
- Nikkaji
- J298.634E
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 965
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Melting Point330 - 335 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 331 · 331-333°C
- Boiling point
- 492.11 °C · 492.11°C (rough estimate)
- Density
- 0.9967 · 0.9967 (rough estimate)
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 4.71 · 4.71±0.70(Predicted)
- color
- White to Off-White
- InChIKey
- MPDGHEJMBKOTSU-PMTKVOBESA-N
- SMILES
- [H][C@]12C[C@](C)(CC[C@]1(C)CC[C@]3(C)C2=CC(=O)C4[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O
- LogP
- 6.57 · 6.570 (est)
- CAS DataBase Reference
- 1449 · 1449-05-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 NYL2CP2E · X6NYL2CP2E
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- ection
- WGK Germany
- 3 · 3
- RTECS
- 190000 · RK0190000
- HS Code
- 29189900 · 29189900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationOlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,18.alpha.,20.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- RK0190000
- hs_code
- 29189900
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- ection
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesSweeteners; sweetness improving agents; flavor enhancers (dairy products, cocoa products, egg products, mutton), flavoring agents (function well especially when used in combination with salt), Chinese folk mostly use it in sauce and sauce products, pickled goods and so on.
Uses18α-Glycyrrhetinic acid may be used to synthesize:3-keto-18α-glycyrrhetinic acid methyl esters of 18α-glycyrrhetinic acidmethyl esters of 3-keto-18α-glycyrrhetinic acid
General Description18α-Glycyrrhetinic acid (18α-GA) is a bioactive triterpenoid found in licorice. It shows selective inhibition of 11-HSD1 (11-hydroxysteroid dehydrogenase 1). It also shows anti-proliferative and apoptotic effect on hepatic stellate cells (HSCs).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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