Baohuoside I supplier | CasNO.113558-15-9

Name
Baohuoside I
EINECS
CAS No. 113558-15-9
Article Data17
CAS DataBase
Density 1.46 g/cm³
Solubility
Melting Point 202-203 °C
Formula C₂₇H₃₀O₁₀
Boiling Point 759.4 °C at 760 mmHg
Molecular Weight 514.529
Flash Point 253.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-(9CI);Baohuoside 1;Baohuoside I;Baohuside I;Icariin II;Icariside II;
PSA 159.05000
LogP 2.59480

Synthetic route

: 489-32-7
icariin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With Cunninghamella blakesleana In methanol for 120h; Microbiological reaction; regioselective reaction;	95.1%
With cellulase In dimethyl sulfoxide at 37℃; pH=5.7; Enzymatic reaction;	84%
With β-glucanase; sodium acetate In aq. buffer at 50℃; for 5h; Enzymatic reaction;	79%

: C15H24N2O17P2

: 118525-40-9
icaritin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With recombinant rhamnosyl transferase from Epimedium pseudowushanense; UDP-rhamnose synthase from Epimedium pseudowushanense; nicotinamide adenine dinucleotide; NADPH In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Enzymatic reaction; regioselective reaction;	87%

: icariin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With hydrogenchloride; sodium acetate In ethanol; water at 50℃; for 5h; pH=5; Enzymatic reaction;	79%

icariin: icariin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With emulsin

epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of: epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of

A: 118525-40-9
icaritin

B: 113558-15-9
icariside II

C: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions

Conditions	Yield
With hydrogenchloride; methanol; water at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With sodium methylate In pyridine at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With acetic acid; β-glucuronidase; naringinase; hesperidinase; β-galactosidase; cellulase; amyloglucosidase at 37℃; for 48h; pH=4.5; Product distribution / selectivity;
Stage #1: epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of With water at 121℃; for 0.5h; Stage #2: at 30℃; for 120h; Product distribution / selectivity;

...Expand

: 518-82-1
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

: 489-32-7
icariin

A: 23313-21-5
anthraglycoside B

B: 113558-15-9
icariside II

Conditions

Conditions	Yield
With glycosyltransferase from Carthamus tinctorius (L.) (Honghua) recombinant; UDP; Cleland's reagent In aq. buffer at 30℃; for 12h; pH=7.4; Enzymatic reaction; regiospecific reaction;	A 26 %Chromat. B 24 %Chromat.

...Expand

: icariin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With GH1 thermostable putative β-glucosidase IagBgl1 from Ignisphaera aggregans at 90℃; for 1.5h; pH=6.5; Temperature; Concentration; pH-value; Enzymatic reaction;

: 113558-15-9
icariside II

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%

: 629-03-8
1 ,6-dibromohexane

: 113558-15-9
icariside II

: 7-((6-bromohexyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	63%

: 113558-15-9
icariside II

: 540-51-2
2-bromoethanol

: 827320-51-4
5-hydroxy-7-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 8h; Reflux;	55%
With potassium carbonate In acetone Reflux; Inert atmosphere;	30%

: 133-89-1
UDP-glucose

: 113558-15-9
icariside II

: 489-32-7
icariin

Conditions

Conditions	Yield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; pH-value; Green chemistry; Enzymatic reaction; regiospecific reaction;	32.8%

: 113558-15-9
icariside II

: 540-51-2
2-bromoethanol

: 1067198-74-6
5-hydroxy-3,7-bis(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 8h; Reflux;	20.2%

: 113558-15-9
icariside II

: 528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7
uridine 5'-diphospho-N-acetylglucosamine

: 7-O-β-D-[2-(N-acetylamino)-2-deoxyglucopyranosyl]baohuoside

Conditions

Conditions	Yield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Green chemistry; Enzymatic reaction;	19.7%

: β-dimethylaminoethyl chloride hydrochloride

: 113558-15-9
icariside II

: 7-(2-dimethylaminoethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	16.7%

: 3616-06-6
UDP-xylose

: 113558-15-9
icariside II

: 7-O-β-D-xylosylbaohuoside

Conditions

Conditions	Yield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Green chemistry; Enzymatic reaction;	6%

: 118525-40-9
icaritin

: 113558-15-9
icariside II

: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
2,3,4,5,6-pentahydroxy-hexanal

Conditions

Conditions	Yield
With methanol In chloroform Purification / work up; Column chromatography;

...Expand

: 118525-40-9
icaritin

: 113558-15-9
icariside II

: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

: rhamnose

Conditions

Conditions	Yield
With methanol In chloroform Purification / work up; Column chromatography;

...Expand

: 113558-15-9
icariside II

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3-yl)oxy)methyl)phosphonic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux 3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere View Scheme

: 113558-15-9
icariside II

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate disodium

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux 3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h / 20 °C / Cooling with ice View Scheme

: 113558-15-9
icariside II

: 6(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methyl))bis(phosphonic acid diethyl ester)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux View Scheme

: 113558-15-9
icariside II

: (((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonate sodium

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux 3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere 4: sodium hydroxide / methanol / 0.5 h View Scheme

: 113558-15-9
icariside II

: (((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux 3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere View Scheme

: 113558-15-9
icariside II

: (2S)-2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)-3-methylbutanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C View Scheme

: 113558-15-9
icariside II

: 2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)acetic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C View Scheme

: 113558-15-9
icariside II

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate diethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: caesium carbonate / acetone / Inert atmosphere; Reflux View Scheme

: 113558-15-9
icariside II

: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-((6-morpholin4-yl)hexyloxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux; Inert atmosphere 2: tetrahydrofuran / Reflux; Inert atmosphere View Scheme

: 89583-07-3
N-(2-bromoethyl)morpholine

: 113558-15-9
icariside II

: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(2-morpholinoethoxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	100 mg

Reaxys ID: 31529750: Reaxys ID: 31529750

: 113558-15-9
icariside II

Reaxys ID: 31529749: Reaxys ID: 31529749

: 113558-15-9
icariside II

: 3,7-bis(2-(dimethylamino)ethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: potassium carbonate / acetone / Reflux; Inert atmosphere View Scheme

: 113558-15-9
icariside II

: 5-hydroxy-3,7-bis(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol; water / 5 h / 50 °C 2: potassium carbonate / acetone / Reflux; Inert atmosphere View Scheme

Baohuoside I Specification

This chemical is called Baohuoside I, and its systematic name is 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl 6-deoxy-α-L-mannopyranoside. With the molecular formula of C₂₇H₃₀O₁₀, its molecular weight is 514.52. The CAS registry number of this chemical is 113558-15-9.

Other characteristics of Baohuoside I can be summarised as followings: (1)ACD/LogP: 4.65; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 4.57; (4)ACD/LogD (pH 7.4): 3.35; (5)ACD/BCF (pH 5.5): 1681.08; (6)ACD/BCF (pH 7.4): 101.99; (7)ACD/KOC (pH 5.5): 6741.99; (8)ACD/KOC (pH 7.4): 409.04; (9)#H bond acceptors: 10; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 100.14 Å²; (13)Index of Refraction: 1.666; (14)Molar Refractivity: 130.58 cm³; (15)Molar Volume: 351.1 cm³; (16)Polarizability: 51.76×10^-24cm³; (17)Surface Tension: 75.7 dyne/cm; (18)Density: 1.46 g/cm³; (19)Flash Point: 253.8 °C; (20)Enthalpy of Vaporization: 116.07 kJ/mol; (21)Boiling Point: 759.4 °C at 760 mmHg; (22)Vapour Pressure: 3.07E-24 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: O=C2C(\O[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)=C(/Oc3c(c(O)cc(O)c23)C\C=C(/C)C)c4ccc(OC)cc4
2.InChI: InChI=1/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
3.InChIKey: NGMYNFJANBHLKA-LVKFHIPRBY
4.Std. InChI: InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
5.Std. InChIKey: NGMYNFJANBHLKA-LVKFHIPRSA-N

Product Name

Baohuoside I

Synthetic route

Baohuoside I Specification

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