Name: Brassinolide
SKU: 72962-43-7

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Basic Information

Molecular Structure:
CAS No.:	72962-43-7
Name:	Brassinolide

Formula:	C₂₈H₄₈O₆
Molecular Weight:	480.686
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;
Density:	1.142 g/cm³
Melting Point:	200-204 °C
Boiling Point:	633.716 °C at 760 mmHg
Flash Point:	202.262 °C
Solubility:	soluble in methanol, ethanol, acetone and tetrahydrofuran
Appearance:	Off-White Solid
Safety:	24/25
PSA:	107.22000
LogP:	3.39000

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

10547-89-4

80736-41-0

19967-55-6

563-80-4

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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

72962-43-7

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Specification