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Epibrassinolide

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Epibrassinolide Basic information

Product Name:
Epibrassinolide
Synonyms:
  • 22R,23R,24R-2ALPHA,3ALPHA,22,28-TETRAHYDROXY-B-HOMO-7-OXA-5ALPHA-ERGOSTA-6-ONE
  • (22R,23R,24R)-2-ALPHA,3-ALPHA,22,23-TETRAHYDROXY-24-METHYL-B-HOMO-7-OXA-5-ALPHA-CHOLESTAN-6-ONE
  • 22R,23R,24R-2A,3A,22,23-TETRAHYDROXY-B-HOMO-7-OXA-5A-ERGOSTAN-6-ONE
  • 24R-BRASSINOLIDE
  • CS-1258
  • 24-EPIBRASSINOLIDE;B1105;BP55
  • B1105
  • BP55
CAS:
78821-43-9
MF:
C28H48O6
MW:
480.68
EINECS:
639-387-1
Product Categories:
  • Steriod
  • Bio-Pesticide
  • Steroids & Hormones - 13C & 2H
  • PLANT GROWTH REGULATOR
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
Mol File:
78821-43-9.mol
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Epibrassinolide Chemical Properties

Melting point:
256°C
Boiling point:
633.7±55.0 °C(Predicted)
Density 
1.141±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly)
form 
Solid
pka
14.27±0.70(Predicted)
color 
White to Off-White
EPA Substance Registry System
3H-Benz[c]indeno[5,4-e]oxepin-3-one, 10-[(1S,2R,3R,4R)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-, (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)- (78821-43-9)
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Safety Information

Risk Statements 
22-36/37/38
Safety Statements 
22-36/37/39-45
WGK Germany 
3
HS Code 
29372900

MSDS

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Epibrassinolide Usage And Synthesis

Description

Epibrassinolide is a brassinosteroid that can be isolated from various plants and has been shown to decrease toxicity and stimulate healthy plant growth in plants under stress. Epibrassinolide is also reported to be a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth. It has also been shown to protect neuronal PC12 cells from 1-methyl-4-phenylpyridinium-induced oxidative stress and consequent apoptosis in dopaminergic neurons.

Chemical Properties

The solubility of epibrassinolide in ethanol and DMSO is approximately 3 mg/ml and approximately 5 mg/ml in DMF.

Chemical Properties

White Solid

Uses

A plant growth stimulant

Uses

Epibrassinolide has been used:

  • in Murashige and Skoog (MS) medium to study the cotyledon and shoot length response of Cappelle-Desprez (rht8) and RIL6 (Rht8) plants towards it
  • in callus-inducing medium for callus induction
  • to induce the expression of the gene leaf inclination 2 (LC2) in rice sampling

Definition

ChEBI: 24-epi-brassinolide is a 2alpha-hydroxy steroid, a 3alpha-hydroxy steroid, a 22-hydroxy steroid, a 23-hydroxy steroid and a brassinosteroid.

Metabolic pathway

Two isomeric metabolites, 25-b- and 26-b-D- glucopyranosyloxy-24-epi-brassinolides, are formed in tomato cell suspension cultures with endogenously applied 24-epi-brassinolide. The two-step metabolic process involves hydroxylation of the side chain at C25 and C26, respectively, followed by glucosidation of the newly formed hydroxyl groups. The ratio between both metabolites is altered by in vivo treatment of the cell cultures with various cytochrome P-450-specific inhibitors, indicating the involvement of two different enzyme systems. Biosynthetically prepared 25-hydroxy-24-epi-brassinolide, reapplied to the cell cultures, is exclusively glucosylated at the 25- hydroxyl group, strongly suggesting regiospecificity of the corresponding glucosyltransferase.

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