Bryonolic acid , CAS No.24480-45-3

CAS: 24480-45-3 Cat. No.: B650492 Formula: C₃₀H₄₈O₃ Molecular Weight: 456.70 PubChem CID: 159970

Synonyms

3beta-Hydroxy-D-C-friedoolean-8-en-29-oic acid | ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl?benzoate | D:C-FRIEDOOLEAN-8-EN-29-OIC ACID, 3-HYDROXY-, (3.BETA.,20.BETA.)- | (2S,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

Synonyms

3beta-Hydroxy-D-C-friedoolean-8-en-29-oic acid | ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl?benzoate | D:C-FRIEDOOLEAN-8-EN-29-OIC ACID, 3-HYDROXY-, (3.BETA.,20.BETA.)- | (2S,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,

Biochemical and Physiological Mechanisms

Bryonolic acid is an active triterpenoid compound with immunomodulatory, anti-inflammatory, antioxidant and anticancer activities.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

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

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols

• 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• 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

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 24480-45-3, the molecular formula is C30H48O3, and the molecular weight is 456.70 g/mol. InChIKey BHVJSLPLFOAMEV-UHIFYLTQSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.