54835-70-0

Basic information

• Product Name: roseoside
• Synonyms: -Dglucopyranosyloxy)- 1-butenyl]-4-hydroxy-3,5,- 5-triMethyl-,(4S)-;roseoside;(4S)-3-Methyl-4-hydroxy-4-[(1E,3R)-3-(β-D-glucopyranosyloxy)-1-butenyl]-5,5-dimethyl-2-cyclohexene-1-one;(S)-4-[(R,E)-3-(β-D-Glucopyranosyloxy)-1-butenyl]-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one;[(1R,2E)-1-Methyl-3-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexenyl]-2-propenyl]β-D-glucopyranoside;Roseoside A;Vomifoliol 9-glucoside;2-Cyclohexen-1-one,4-[(1E,3R)-3-(â
• CAS NO: 54835-70-0
• Molecular Formula: C₁₉H₃₀O₈
• Molecular Weight: 386.4367
• Mol File: 54835-70-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 595.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 12.52±0.60(Predicted)
• CAS DataBase Reference: roseoside(CAS DataBase Reference)
• NIST Chemistry Reference: roseoside(54835-70-0)
• EPA Substance Registry System: roseoside(54835-70-0)

Safety Data

• Hazardous Substances Data: 54835-70-0(Hazardous Substances Data)

Synthetic route

(6S,9R)-9-(4,6-O-isopropylidene-β-D-glucopyranosyl)oxy-6-hydroxy-3-oxo-α-ionol → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
With water; pyridinium p-toluenesulfonate In ethanol at 20 - 50℃; for 22h;	99%

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-[(E)-(R)-3-((S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyloxy]-tetrahydro-pyran-3-yl ester (863032-39-7) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
With methanol; lithium hydroxide at 20℃; for 24h;	83%

tetraacetylroseoside (54619-16-8) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
With sodium methylate In methanol for 2h; Ambient temperature;	7 mg
With sodium methylate

vomifoliol acetate (84551-74-6) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 2: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 3: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

Acetic acid (E)-(R)-1-methyl-3-((1S,6R)-2,2,6-trimethyl-4-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-allyl ester (437711-51-8) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 2: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 3: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 4: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

Acetic acid (E)-(R)-3-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-1-methyl-allyl ester (863032-35-3) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 2: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 3: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 4: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 5: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

(E)-(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol (863032-50-2) → (6S,9R)-roseoside (54835-70-0)

Conditions

Yield

Multi-step reaction with 8 steps 1: 90 percent / pyridine / 3 h / 20 °C 2: 30 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 20 °C 3: 97 percent / HF*Py / tetrahydrofuran / 0.25 h / 0 °C 4: Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 5: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 6: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 7: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 8: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

Acetic acid (E)-(R)-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-1-methyl-allyl ester (872003-41-3) → (6S,9R)-roseoside (54835-70-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 30 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 20 °C 2: 97 percent / HF*Py / tetrahydrofuran / 0.25 h / 0 °C 3: Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 4: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 5: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 6: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 7: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

Acetic acid (E)-(R)-3-[(1S,4S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-1-methyl-allyl ester (863032-34-2) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 97 percent / HF*Py / tetrahydrofuran / 0.25 h / 0 °C 2: Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 3: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 4: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 5: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 6: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

blumenol A (23526-45-6) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 2: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (81058-27-7) → (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 2: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-yn-2-ol (322474-92-0) → (6S,9R)-roseoside (54835-70-0)

Conditions

Yield

Multi-step reaction with 9 steps 1: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / 60 °C 2: 90 percent / pyridine / 3 h / 20 °C 3: 30 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 20 °C 4: 97 percent / HF*Py / tetrahydrofuran / 0.25 h / 0 °C 5: Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 6: 446 mg / p-TsOH*H2O / benzene / 17 h / 20 °C 7: 85 percent / NaOMe; MeOH / 1.5 h / 20 °C 8: 57 percent / N,N-tetramethylurea; AgOTf / CH2Cl2 / 1.83 h / 0 - 20 °C 9: 83 percent / LiOH*H2O; MeOH / 24 h / 20 °C View Scheme

6'-O-caffeoyl-(6S,9R)-roseoside → D-glucose (50-99-7) + blumenol A (23526-45-6) + caffeic acid (331-39-5) + (6S,9R)-roseoside (54835-70-0)

Conditions	Yield
With cellulase In water at 37℃; for 12h; Enzymatic reaction;	A n/a B 0.5 mg C n/a D 1 mg

(6S,9R)-roseoside (54835-70-0) → D-glucose (50-99-7) + blumenol A (23526-45-6)

Conditions	Yield
With water at 37℃; for 2h; enzyme: hesperidinase;	A 11 mg B 10 mg

(6S,9R)-roseoside (54835-70-0) → 6,9-dihydroxymegastigma-4,7-dien-3-one (23526-45-6, 24427-77-8, 50763-72-9, 50763-73-0)

Conditions	Yield
In water for 16h; Ambient temperature; β-glucosidase;	1.2 mg

(6S,9R)-roseoside (54835-70-0) → tetraacetylroseoside (54619-16-8)

Conditions	Yield
	12 mg

acetic anhydride (108-24-7) + (6S,9R)-roseoside (54835-70-0) → tetraacetylroseoside (54619-16-8)

Conditions	Yield
In pyridine for 24h; Ambient temperature;	17 mg

(6S,9R)-roseoside (54835-70-0) → blumenol A (23526-45-6)

Conditions	Yield
With β-glucosidase at 37℃; for 48h; pH 5.0 (acetate buffer);	11 mg

Upstream product

• 54835-69-7 3,4-Dihydro-3,6,8-trihydroxy-3-pentadecyl-1H-2-benzopyran-1-one 
• 54835-68-6 2-(2,4-Dihydroxyphenyl)-3-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one 
• 54835-67-5 2-(2,4-Dihydroxyphenyl)-3-(3,7-dimethyl-2,6-octadienyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one 
• 54835-66-4 8-(2,4-Dihydroxyphenyl)-7-(3,7-dimethyl-2,6-octadienyl)-5-hydroxy-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one 
• 54835-65-3 [(1aS)-1a,1bα,2,5a,6,6aβ-Hexahydro-5aα,6α-dihydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2α-yl]β-D-glucopyranoside 
• 54835-64-2 Daphneolone 
• 548-35-6 TRUXENE 
• 54835-57-3 pentacyclo[15.3.1.1~4,8~.1~7,11~.1~14,18~]tetracosa-1(21),4(24),5,7,9,11(23),14(22),15,17,19-decaene (non-preferred name) 
• 5483-53-4 (5E)-5-[4-(benzyloxy)-3-ethoxybenzylidene]-3-phenyl-2-thioxo-1,3-thiazolidin-4-one 
• 5483-48-7 N-(4-nitrophenyl)-alpha-D-arabinofuranosylamine 
• 5483-45-4 ethyl 2-(2-chloro-4-{[(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)imino]methyl}phenoxy)propanoate 
• 54833-79-3 1-Acetyl-2-methyl-5,5-diphenyl-4-imidazolidinone 
• 54833-78-2 N-[2-(1,2-Dihydro-1-hydroxy-2-oxoquinolin-3-yl)phenyl]acetamide 
• 54833-77-1 3-(4-Nitrobenzylidene)-5-phenylfuran-2(3H)-one 

Downstream Products

• 54835-71-1 (2S,3R)-2-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl beta-D-glucopyranoside 
• 54835-74-4 (1R,2R,3S,6R,7S)-7-(1,3-benzodioxol-5-yl)-1,3-dimethoxy-6-methyl-5-(prop-2-en-1-yl)bicyclo[3.2.1]octane-2,8-diol 
• 54835-75-5 Phacidin 
• 54835-85-7 2,3,5-trichloro-6-[(E)-2-(diethylamino)ethenyl]cyclohexa-2,5-diene-1,4-dione 
• 5483-61-4 4-methyl-6-[(2,2,3,3,4,4,5,5-octafluoropentyl)oxy]pyrimidin-2-amine 
• 5483-65-8 (Z)-N-(3,3-dimethyl-5-oxocyclohexylidene)glycine 
• 54836-75-8 1,3,4-Thiadiazol-2-amine, 5-methoxy-N-methyl- 
• 54836-90-7 (S)-α-Amino-4-carboxy-3-furanpropionic acid 
• 5483-69-2 2-[(3,5-dimethyl-1H-pyrazol-4-yl)sulfanyl]-N-[(E)-phenylmethylidene]aniline 
• 54836-96-3 α-Amino-2-carboxy-1-azetidinebutanoic acid 
• 54837-08-0 Alanine, N-methoxy- (9CI) 
• 54837-12-6 Alanine, N-(1-methylpropoxy)- (9CI) 
• 54837-13-7 Alanine, N-(1,1-dimethylethoxy)- (9CI) 
• 54837-14-8 N-(benzyloxy)glycine 

Recommend Products

• 108-24-7  acetic anhydride 
• 54619-16-8  tetraacetylroseoside 
• 863032-39-7  2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-[(E)-(R)-3-((S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyloxy]-tetrahydro-pyran-3-yl ester 
• 50-99-7  D-glucose 
• 23526-45-6  blumenol A 
• 331-39-5  caffeic acid 
• 437711-51-8  Acetic acid (E)-(R)-1-methyl-3-((1S,6R)-2,2,6-trimethyl-4-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-allyl ester 
• 84551-74-6  vomifoliol acetate 
• 863032-48-8  2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-[(E)-(S)-3-((S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyloxy]-tetrahydro-pyran-3-yl ester 
• 863032-38-6  Acetic acid (E)-(R)-3-((R)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyl ester 
• 863032-32-0  (6R,9R)-vomifoliol 
• 863032-40-0  2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-[(E)-(R)-3-((R)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyloxy]-tetrahydro-pyran-3-yl ester 
• 54619-16-8  roseoside tetraacetate 
• 322474-92-0  (R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-yn-2-ol