72962-43-7 Usage
Chemical Properties
Off-White Solid
Uses
Different sources of media describe the Uses of 72962-43-7 differently. You can refer to the following data:
1. Brassinolide can be used as plant growth regulator.
2. Plant growth regulator.
3. Brassinolide has been used as a plant growth hormone.
General Description
Brassinolide is a plant growth hormone and the most biologically active brassinosteroid (BR). It has been implicated in Auxin signaling. It has also been used for studying plant biosynthetic pathways. Brassinolide might also regulate water-transport properties of cell membranes in Arabidopsis thaliana.
Biological Activity
brassinolide is a plant growth regulator. plant growth regulators are naturally produced by plants and are critical for regulating their own growth. plant growth regulators act via modifying or controlling plant growth processes, such as leave and flower formation, stem elongation, as well as fruit development and ripening.
Biochem/physiol Actions
Brassinolide is a plant growth hormone that has been implicated in Auxin signaling. It has also been used for studying plant biosynthetic pathways.
in vitro
brassinolide induced the time and concentration-dependent cytotoxicity in pc-3 cells. the mode of such cell death appeared to be apoptosis predominately, as demonstrated by fluorescence, flow-cytometric analyses and transmission electron microscopes. moreover, caspase-3 activity was increased after brassinolide treatment obviously. western blot studies showed brassinolide treatment triggered a time-dependent decrease in the expression of bcl-2 [1].
in vivo
brassinolide had the similar function of reducing the blood glucose levels as phenformin, but without the dose-dependent manner. the blood glucose levels showed significant differences after brassinolide treatment with different doses (200, 100, and 50 mg/kg). these results indicated that brassinolide could reduce the blood glucose levels without toxicity [2].
references
[1] wu yd,lou yj. brassinolide, a plant sterol from pollen of brassica napus l., induces apoptosis in human prostate cancer pc-3 cells. pharmazie.2007 may;62(5):392-5.[2] chen shi-ping, he jia, wang qi-jing, wang jian-dong, ye yan-li, xian li-jian. effect of brassinolide on levels of blood glucose in alloxan—induced diabetes rats. acta metallurgica sinica, 2009,v26(03): 21-23
Check Digit Verification of cas no
The CAS Registry Mumber 72962-43-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,2,9,6 and 2 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 72962-43:
(7*7)+(6*2)+(5*9)+(4*6)+(3*2)+(2*4)+(1*3)=147
147 % 10 = 7
So 72962-43-7 is a valid CAS Registry Number.
InChI:InChI=1/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16+,17+,18?,19+,20+,21-,22+,23-,24-,25+,27-,28-/m1/s1
72962-43-7Relevant articles and documents
A Novel Synthesis of Brassinolide and Related Compounds
Wei-Shan, Zhou,Jiang, Biao,Pan, Xin-fu
, p. 612 - 613 (1989)
A stereoselective synthesis of the natural promoting steroids, brassinolide, homobrassinolide, and typhasterol is described, which involves construction of a side chain by lactonisation of Z-(5) under acidid conditions to give an α,β-unsaturated δ-lactone (6) with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.
STEREOSELECTIVE SYNTHESIS OF THE BRASSINOLIDE SIDE CHAIN: NOVEL SYNTHESIS OF BRASSINOLIDE AND RELATED COMPOUNDS
Zhou, Wei-shan,Jiang, Biao,Pan, Xin-fu
, p. 3173 - 3188 (1990)
A stereoselective synthesis of the brassinolide side chain involves the lactonization of Z-10 under acidic condition to give an α,β-unsaturated-δ-lactone 11 with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.The 22R,23R,24R-γ-hydroxy-δ-lactone 14 was used as key intermediate for the syntheses of brassinolide (1), homobrassinolide (2), and typhasterol (4) as well as the side chain of the dolicholide (3).
A general approach to synthesis of labeled brassinosteroids: Preparation of [25,26,27-2h7]brassinolide with 60% isotopic purity from the parent brassinolide
Seto, Hideharu,Fujioka, Shozo,Koshino, Hiroyuki,Yoshida, Shigeo,Watanabe, Tsuyoshi,Takatsuto, Suguru
, p. 7525 - 7528 (2007/10/03)
From brassinolide (BL) 1, [25,26,27-2H(n)]BL 10 was synthesized in 5 steps including C-25 hydroxylation, dehydration and catalytic deuteriogenation. In direct oxy-functionalization of tetra-O-acetyl BL 2 with methyl(trifluoromethyl)dioxirane leading to 25-hydroxyl compound 3, 14- hydroxyl, 25-hydroxy-15-oxo and 14,25-dihydroxyl derivatives, 4, 5 and 6, were newly identified; the catalytic deuteriogenation of Δ(25(26))-BL 8 using 5% palladium-on-charcoal resulted in abundant incorporation of deuterium atoms to give 10 with 60% isotopic purity of [25,26,27-2H7]BL.
Improved synthesis of brassinolide
McMorris, Trevor C.,Chavez, Rodrigo G.,Patil, Prakash A.
, p. 295 - 302 (2007/10/03)
Brassinolide has been synthesized from stigmasterol in an overall yield of 7%. The key step in the synthesis is aldol condensation of 2α,3α-isopropylidenedioxy-6-oxo-23,24-dinor-5α-cholan-22-al with 3-isopropylbut-2-enolide carried out at -78°C, which gives a product with 22R,23R stereochemistry in high yield. Catalytic hydrogenation of this product is highly stereoselective leading to the desired 245 stereochemistry in an intermediate which is readily transformed into brassinolide. Copyright 1996 by the Royal Society of Chemistry.