Brassicasterol - ≥97% , CAS No.474-67-9

CAS: 474-67-9 Cat. No.: B136332 Molecular Weight: 398.66 EC Number: 207-486-5

GRADE & PURITY ≥97%

Synonyms

24(R)-Methylcholesta-5,22E-dien-3beta-ol | CHEBI:3168 | EINECS 207-486-5 | C08813 | Ergosta-5,22-dien-3-ol, (3b,22E)- | Q2700587 | (3.BETA.,22E)-ERGOSTA-5,22-DIEN-3-OL | AKOS040760305 | DTXSID80197124 | Ergosta-5,22E-dien-3beta-ol | E80559 | Brassicasteri

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease.

Specifications

Synonyms

24(R)-Methylcholesta-5, 22E-dien-3beta-ol | CHEBI:3168 | EINECS 207-486-5 | C08813 | Ergosta-5, 22-dien-3-ol, (3b, 22E)- | Q2700587 | (3.BETA., 22E)-ERGOSTA-5, 22-DIEN-3-OL | AKOS040760305 | DTXSID80197124 | Ergosta-5, 22E-dien-3beta-ol | E80559 | Brassicasteri

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

Campesterol is a plant sterol with a structure similar to cholesterol. Phytosterols compete with cholesterol, reducing the amount of cholesterol incorporated into micelles and thus reducing its absorption. Brassicae sterol has been reported to slow the pr

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504763348
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763348
• Canonical Smiles: CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• InChIKey: OILXMJHPFNGGTO-ZAUYPBDWSA-N
• INCHI: 1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• WGK Germany: 3
• Molecular Weight: 398.66
• Reaxy-Rn: 2337874
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2337874&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Ergostane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Ergostane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Ergosterols and derivatives
• Alternative Parents: 3-beta-hydroxysteroids 3-beta-hydroxy delta-5-steroids Delta-5-steroids Secondary alcohols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Ergosterol-skeleton - 3-beta-hydroxysteroid - 3-beta-hydroxy-delta-5-steroid - Hydroxysteroid - 3-hydroxysteroid - 3-hydroxy-delta-5-steroid - Delta-5-steroid - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
• External Descriptors: Ergosterols and C24-methyl derivatives

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

• Sensitivity: Light sensitive
• Molecular Weight: 398.700 g/mol
• XLogP3: 8.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 398.355 Da
• Monoisotopic Mass: 398.355 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 659.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Zihan Xu, Shanshan Liu, Mingyue Shen, Jianhua Xie, Jun Yang.  (2021)  Evaluation of trans fatty acids, carbonyl compounds and bioactive minor components in commercial linseed oils.  FOOD CHEMISTRY,      [PMID:34469834] [10.1016/j.foodchem.2021.130930]

2. Liu Shanshan, Hu Huiyu, Yu Yanpeng, Zhao Jiahui, Liu Lichun, Zhao Shanshan, Xie Jianhua, Li Chang, Shen Mingyue.  (2021)  Simultaneous Determination of Tocopherols, Phytosterols, and Squalene in Vegetable Oils by High Performance Liquid Chromatography-Tandem Mass Spectrometry.  Food Analytical Methods,  14  (8): (1567-1576).  [PMID:] [10.1007/s12161-021-01987-5]