for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Bryonolic acid is an active triterpenoid compound with immunomodulatory, anti-inflammatory, antioxidant and anticancer activities .
In Vitro
Bryonolic acid exerts anti-allergic activity by inhibiting homologous passive cutaneous anaphylaxis and delayed hypersensitivity. Bryonolic acid reduces nitric oxide by suppressing inducible nitric oxide synthase expression, indicating anti-inflammatory activity. In rat adrenal pheochromocytoma (PC12) cells, Bryonolic acid against N-methyl-D-aspartate (NMDA)-induced neurotoxicity, indicating it as a candidate neuroprotective agent for cerebral ischemic treatment. Bryonolic acid (1-200 μM) inhibits acyl-coA: cholesterol acyl transferase (ACAT) activity in rat liver microsomes in a concentration-dependent manner, blocking the biosynthesis of the cholesterol fatty acid ester tumour promoter. Bryonolic acid inhibits ACAT in intact cancer cells with an IC 50 of 12.6 µM. Bryonolic acid inhibits both clonogenicity and invasiveness in MCF-7 MB-231, U87 and 3T3-EA cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Bryonolic acid (500 mg/kg; i.p.; once) potently induces HO-1 in a manner dependent on the Nrf2-Keap1 pathway. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Wild-type and Nrf2-/- miceDosage: 500 mg/kg Administration: i.p.; once Result: Induced HO-1 in a manner dependent on the Nrf2-Keap1 pathway.
| Canonical Smiles | CC1(C2CCC3=C(C2(CCC1O)C)CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C |
|---|---|
| IUPAC Name | (2S,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-2-carboxylic acid |
| InChIKey | BHVJSLPLFOAMEV-UHIFYLTQSA-N |
| INCHI | 1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-23,31H,8-18H2,1-7H3,(H,32,33)/t21-,22+,23-,26+,27-,28+,29+,30-/m0/s1 |
| Isomeric SMILES | C[C@]12CC[C@](C[C@H]1[C@@]3(CCC4=C([C@]3(CC2)C)CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)(C)C(=O)O |
| Alternate CAS | 24480-45-3 |
| PubChem CID | 159970 |
| MeSH Entry Terms | 3beta-hydroxy-D-C-friedoolean-8-en-29-oic acid;bryonolic acid |
| Molecular Weight | 456.70 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Alcohols and polyols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cyclic alcohols and derivatives |
| Alternative Parents | Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Cyclic alcohol - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. |
| External Descriptors | hydroxy monocarboxylic acid - pentacyclic triterpenoid |
| Molecular Weight | 456.700 g/mol |
|---|---|
| XLogP3 | 7.200 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Exact Mass | 456.36 Da |
| Monoisotopic Mass | 456.36 Da |
| Topological Polar Surface Area | 57.500 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 902.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 8 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
