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Brassinolide
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Name

Brassinolide

 EINECS N/A
CAS No. 72962-43-7 Density 1.142 g/cm3
PSA 107.22000 LogP 3.39000
Solubility soluble in methanol, ethanol, acetone and tetrahydrofuran Melting Point 200-204 °C
Formula C28H48O6 Boiling Point 633.716 °C at 760 mmHg
Molecular Weight 480.686 Flash Point 202.262 °C
Transport Information N/A Appearance Off-White Solid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 72962-43-7 (Brassinolide) Hazard Symbols N/A
Synonyms

B-Homo-7-oxaergostan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22R,23R,24S)-;6H-Benz[c]indeno[5,4-e]oxepin-6-one,1-(2,3-dihydroxy-1,4,5-trimethylhexyl)hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-,[1R-[1a(1S*,2R*,3R*,4S*),3ab,3ba,6ab,8b,9b,10aa,10bb,12aa]]-;Brassinolide (BR);Brassinolide;

Article Data 18

Brassinolide Synthetic route

76987-58-1

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Heating;94%
With sodium hydroxide In methanol; water for 3h; Heating;57%
With hydrogenchloride; methanol; potassium hydroxide 1.) reflux, 1 h, 2.) room temperature, 1 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: NaOH
2: HCl
View Scheme
83066-72-2

(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one

A

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide In dichloromethane at 22℃; for 1h;A 74%
B n/a
91708-76-8

(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide; trifluoroacetic acid In chloroform for 3h; Ambient temperature;53%
Multi-step reaction with 3 steps
1: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
2: pyridine, N,N-dimethylaminopyridine
View Scheme
124853-28-7

3-dehydroteasterone

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With amalgamated zinc; osmium(VIII) oxide; chloro-trimethyl-silane; trifluoroacetyl peroxide; 4-methylmorpholine N-oxide 1.) THF, rt., 12 h; 2.) THF, aq. t-BuOH; 3.) CH2Cl2; Yield given. Multistep reaction;
80736-41-0

castasterone

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: pyridine, N,N-dimethylaminopyridine
View Scheme
77027-48-6

2,3,22,23-tetra-O-acetylcastasterone

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
106315-18-8

Acetic acid (1R,2R,3S)-2-acetoxy-1-[(S)-1-((1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8,9-dihydroxy-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-1-yl)-ethyl]-3,4-dimethyl-pentyl ester

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol for 3h; Heating;1.79 g

(1S,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4,5-dihydroxy-2-methyl-cyclohexanecarboxylic acid

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With hydrogenchloride
111118-49-1

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

A

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
81481-15-4

(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde

72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) n-BuLi, 2.) 30percent H2O2 / 1.) THF, -78 deg C, 3 h, 2.) acetic acid, room temperature, 15 h
2: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C
3: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
4: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
3: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
4: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
5: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
6: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
7: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 7 steps
1: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
3: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
4: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
5: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
6: pyridine, N,N-dimethylaminopyridine
View Scheme

Brassinolide Specification

The Brassinolide, with the CAS registry number 72962-43-7, is also known as B-Homo-7-oxaergostan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22R,23R,24S)-. It belongs to the product categories of Bio-Pesticide; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. This chemical's molecular formula is C28H48O6 and molecular weight is 480.68. What's more, its systematic name is (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one. Its classification codes are: (1)Growth Substances; (2)Plant Growth Regulators. This chemical is a plant hormone. The first isolated brassinosteroid, it was discovered when it was shown that pollen from rapeseed (Brassica napus) could promote stem elongation and cell division. The biologically active component was isolated and named brassinolide.

Physical properties of Brassinolide are: (1)ACD/LogP: 3.471; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.47; (4)ACD/LogD (pH 7.4): 3.47; (5)ACD/BCF (pH 5.5): 255.94; (6)ACD/BCF (pH 7.4): 255.94; (7)ACD/KOC (pH 5.5): 1842.26; (8)ACD/KOC (pH 7.4): 1842.26; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 107.22 Å2; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 131.257 cm3; (15)Molar Volume: 421.056 cm3; (16)Polarizability: 52.035×10-24cm3; (17)Surface Tension: 45.8 dyne/cm; (18)Density: 1.142 g/cm3; (19)Flash Point: 202.262 °C; (20)Enthalpy of Vaporization: 107.343 kJ/mol; (21)Boiling Point: 633.716 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C3OC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]2[C@@]4(C)C[C@@H](O)[C@@H](O)C[C@H]34)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
(2)Std. InChI: InChI=1S/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+/m0/s1
(3)Std. InChIKey: IXVMHGVQKLDRKH-KNBKMWSGSA-N

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