Epibrassinolide
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
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)
Safety Information
- Risk Statements
- 22-36/37/38
- Safety Statements
- 22-36/37/39-45
- WGK Germany
- 3
- HS Code
- 29372900
MSDS
- Language:English Provider:SigmaAldrich
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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