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: 4

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)

Usage

General Description

Roseoside is a natural chemical compound extracted from various plant species, particularly from the family of Rosaceae - which comprises a large number of rose species. It is classified as a flavonoid glycoside, known for its diverse therapeutic properties including antioxidant, anti-inflammatory, and antimicrobial activities. This explains its use in traditional medicine for treatment of various diseases. However, comprehensive and detailed knowledge about its pharmacological effects, potential toxicity, and mechanisms of action remain limited, necessitating further research work in this field.

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

• 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 
• 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 
• 863032-39-7 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 
• 322474-92-0 (R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-yn-2-ol 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 23526-45-6 blumenol A 
• 863032-34-2 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 
• 872003-41-3 Acetic acid (E)-(R)-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-1-methyl-allyl ester 
• 863032-50-2 (E)-(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol 
• 863032-35-3 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 
• 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 
• 54619-16-8 tetraacetylroseoside 
• 737763-66-5 Acetic acid (E)-(S)-3-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-1-methyl-allyl ester 

Downstream Products

• 54619-16-8 roseoside tetraacetate 
• 54619-16-8 tetraacetylroseoside 
• 50-99-7 D-glucose 
• 1186648-59-8 (6S,9S)-6,9-dihydroxymegastiman-4-megastigmen-3-one-9-O-β-D-glucopyranoside 
• 189351-15-3 (6S,7E,9S)-6,9-dihydroxy-4,7-megastigmadien-3-one 
• 23526-45-6 6,9-dihydroxymegastigma-4,7-dien-3-one 
• 23526-45-6 blumenol A 

Relevant articles and documents

A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells

Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers.

Synthesis of optically active vomifoliol and roseoside stereoisomers

A synthesis of optically active vomifoliol stereoisomers 1-4 and their glucosides, roseoside stereoisomers 5-8, was accomplished via α-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of α,β-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also perfomed.