Quillaic acid

Iupac Name：(4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS No.: 631-01-6

Molecular Weight：486.693

Modify Date.: 2023-02-10 02:38

Introduction:

Quillaic acid(Quillaja sapogenin) is the major aglycone of the widely studied saponins of the Chilean indigenous tree Quillaja saponaria Mol; can elicit dose-dependent antinociceptive effects in two murine thermal models.

Quillaic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). It has a role as an anti-inflammatory agent and a metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and an aldehyde. It is a conjugate acid of a quillate. It derives from a hydride of an oleanane.

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1. Names and Identifiers

: 1.1 Name; Quillaic acid; 1.2 Synonyms; (3beta,4alpha,16alpha)-3,16-dihydroxy-23-oxoolean-12-en-28-oic acid (3Β,16α)-3,16-Dihydroxy-23-oxoolean-12-en-28-oic acid (3β,9ξ,16α)-3,16-Dihydroxy-23-oxoolean-12-en-28-oic acid (4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid 3b,16a-Dihydroxy-23-oxoolean-12-en-28-oic Acid EINECS 211-149-8 Olean-12-en-28-oic acid, 3,16-dihydroxy-23-oxo-, (3.beta.,4.alpha.,16.alpha.)- Olean-12-en-28-oic acid, 3,16-dihydroxy-23-oxo-, (3Β,16α)- Olean-12-en-28-oic acid, 3,16-dihydroxy-23-oxo-, (3β,9ξ,16α)- Quillaic acid 631-01-6 Quillaic acid(Quillaja sapogenin) Quillaja sapogenin Quillaja Saponaria Extract Quillajasaeure Saponin bark extract; View all

1.3 CAS No.: 631-01-6

1.4 CID: 101810

1.5 EINECS(EC#): 211-149-8

1.6 Molecular Formula: C30H46O5 (isomer)

1.7 Inchi: InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

1.8 InChIkey: MQUFAARYGOUYEV-UAWZMHPWSA-N

1.9 Canonical Smiles: CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C=O)O)C)C(=O)O)C

1.10 Isomers Smiles: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)O)C)C)(C)C=O)O

2. Properties

2.1 Density: 1.18

2.1 Melting point: 294℃

2.1 Boiling point: 613.3°C at 760 mmHg

2.1 Refractive index: 1.575

2.1 Flash Point: 338.7°C

2.1 Precise Quality: 486.33500

2.1 PSA: 94.83000

2.1 logP: 5.38340

2.1 Solubility: Insuluble (7.8E-4 g/L) (25 oC),

2.2 Color/Form: Powder

2.3 pKa: 4.41±0.70(Predicted)

2.4 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Definition: ChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). Quillaic acidSupplier

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

6. Synthesis Route

631-01-6Total: 3 Synthesis Route

97892-86-9

87-72-9 164 Suppliers

10257-28-0 45 Suppliers

6556-12-3 39 Suppliers

631-01-6 15 Suppliers

Literatures:
Phytochemistry (Elsevier), , vol. 26, # 1 p. 229 - 236
Yield: null

107091-09-8

2280-44-6 3 Suppliers

6556-12-3 39 Suppliers

73-34-7

30738-01-3

73-34-7

631-01-6 15 Suppliers

Literatures:
Phytochemistry (Elsevier), , vol. 26, # 1 p. 229 - 236
Yield: null

1248822-15-2

58-86-6 239 Suppliers

6556-12-3 39 Suppliers

631-01-6 15 Suppliers

Literatures:
Chemical and Pharmaceutical Bulletin, , vol. 58, # 3 p. 412 - 414
Yield: null

7. Other Information

7.0 Mesh Entry Terms: 3 beta,16 alpha-dihydroxy-23-oxoolean-12-en-28-oic acid

7.1 Use Classification: Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]

7.2 Uses: Quillaic Acid an unglycosylated saponin from the Quillaja saponaria bark is used as a topical antiinflammatory.

7.3 Definition: ChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer).

8. Computational chemical data

Molecular Weight: 486.693g/mol
Molecular Formula: C₃₀H₄₆O₅
Compound Is Canonicalized: True
XLogP3-AA: 6.1
Exact Mass: 486.33452456
Monoisotopic Mass: 486.33452456
Complexity: 970
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 94.8
Heavy Atom Count: 35
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4OAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGCAAAAAADAAAAAGgAACAAADxSggAICCAAAAgCIAijSiAAAAAAgAAAACAEAAAgAEBYAAQAAQAAFoAAIAAOIyPCPgAAAAAAAAADAAAYAADAAAAAAAAAAAA==

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