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61276-17-3

61276-17-3

Identification

  • Product Name:Verbascoside

  • CAS Number: 61276-17-3

  • EINECS:

  • Molecular Weight:624.596

  • Molecular Formula: C29H36O15

  • HS Code:29389090

  • Mol File:61276-17-3.mol

Synonyms:b-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl3-O-(6-deoxy-a-L-mannopyranosyl)-,4-[3-(3,4-dihydroxyphenyl)-2-propenoate], (E)-;Acteoside;Kusaginin;NSC603831;Russetinol;TJC 160;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

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  • Manufacture/Brand:TRC
  • Product Description:Verbascoside
  • Packaging:100mg
  • Price:$ 545
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Verbascoside >97.0%(HPLC)
  • Packaging:10mg
  • Price:$ 128
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Verbascoside >97.0%(HPLC)
  • Packaging:50mg
  • Price:$ 449
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Verbascoside ≥99% (HPLC)
  • Packaging:10mg
  • Price:$ 598
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Verbascoside primary pharmaceutical reference standard
  • Packaging:10mg
  • Price:$ 441
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Verbascoside United States Pharmacopeia (USP) Reference Standard
  • Packaging:15mg
  • Price:$ 429
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Verbascoside
  • Packaging:100 mg
  • Price:$ 950
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Verbascoside
  • Packaging:10 mg
  • Price:$ 625
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  • Manufacture/Brand:JR MediChem
  • Product Description:Acteoside(NewProduct) 98%
  • Packaging:1g
  • Price:$ 1280
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  • Manufacture/Brand:JR MediChem
  • Product Description:Acteoside(NewProduct) 98%
  • Packaging:500mg
  • Price:$ 780
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Relevant articles and documentsAll total 8 Articles be found

An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside

Zhang, Xiaojuan,Yang, Yutong,Wang, Fuye,Zhou, Zhengbing,Zhang, Hongbin,Zhu, Yugen

supporting information, p. 9210 - 9215 (2021/11/30)

Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.

Total Synthesis of the Phenylpropanoid Glycoside, Acteoside

Kawada, Toshinari,Asano, Ryuji,Hayashida, Shiho,Sakuno, Tomoyasu

, p. 9268 - 9271 (2007/10/03)

-

NINE PHENETHYL ALCOHOL GLYCOSIDES FROM STACHYS SIEBOLDII

Nishimura, Hiroaki,Sasaki, Hiroshi,Inagaki, Nobuyuki,Chin, Masao,Zhengxiong, Chen,Mitsuhashi, Hiroshi

, p. 965 - 969 (2007/10/02)

Three new phenethyl alcohol glycosides together with six known compounds have been isolated from the leaves of Stachys sieboldii.On the basis of chemical and spectral analyses, the structures of three new compounds named stachysosides A, B and C have been established as 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-caffeoyl-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside and 2-(3-hydroxy-4-methoxyphenyl)ethyl O-α-L-arabinopranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside, respectively.

Process route upstream and downstream products

Process route

3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside
253790-76-0

3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

Conditions
Conditions Yield
With cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; at 40 ℃; for 10h;
44%
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2,3,4-tris-O-triethylsilyl-α-L-rhamnopyranosyl(1→3)-2,6-di-O-triethylsilyl-4-O-(E)-3,4-bis(tert-butyldimethylsilyl)-caffeoyl-β-D-glucopyranoside

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2,3,4-tris-O-triethylsilyl-α-L-rhamnopyranosyl(1→3)-2,6-di-O-triethylsilyl-4-O-(E)-3,4-bis(tert-butyldimethylsilyl)-caffeoyl-β-D-glucopyranoside

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 2h;
87%
2-<3,4-bis(benzyloxy)phenyl>ethanol
96826-11-8

2-<3,4-bis(benzyloxy)phenyl>ethanol

Conditions
Conditions Yield
Multi-step reaction with 10 steps
1: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C
2: 94 percent / sodium methoxide / methanol / 2 h / 20 °C
3: 86 percent / pyridine / 0 - 20 °C
4: 92 percent / pyridine / 0 - 20 °C
5: 79 percent / AcOH / dioxane / 6 h / 110 °C
6: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
7: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
8: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
9: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
10: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; cyclohexa-1,4-diene; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: glycosylation; ortho-esterification / 2: Deacetylation / 3: tritylation / 4: Acetylation / 5: Rearrangement / 6: Esterification / 7: Oxidation / 8: rhamnosylation / 9: Deacetylation / 10: Hydrogenolysis;
(E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid
54429-62-8

(E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
3: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
4: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
5: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With dmap; selenium(IV) oxide; cyclohexa-1,4-diene; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Oxidation / 3: rhamnosylation / 4: Deacetylation / 5: Hydrogenolysis;
acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
39698-00-5

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 11 steps
1: 100 percent / α,α-dichloromethyl methyl ether; ZnCl2*Et2O / CH2Cl2 / 1 h / 20 °C
2: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C
3: 94 percent / sodium methoxide / methanol / 2 h / 20 °C
4: 86 percent / pyridine / 0 - 20 °C
5: 92 percent / pyridine / 0 - 20 °C
6: 79 percent / AcOH / dioxane / 6 h / 110 °C
7: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
8: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
9: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
10: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
11: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; zinc chloride diethyl ether; Dichloromethyl methyl ether; cyclohexa-1,4-diene; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Substitution / 2: glycosylation; ortho-esterification / 3: Deacetylation / 4: tritylation / 5: Acetylation / 6: Rearrangement / 7: Esterification / 8: Oxidation / 9: rhamnosylation / 10: Deacetylation / 11: Hydrogenolysis;
2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl chloride
253790-67-9

2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl chloride

Conditions
Conditions Yield
Multi-step reaction with 10 steps
1: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C
2: 94 percent / sodium methoxide / methanol / 2 h / 20 °C
3: 86 percent / pyridine / 0 - 20 °C
4: 92 percent / pyridine / 0 - 20 °C
5: 79 percent / AcOH / dioxane / 6 h / 110 °C
6: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
7: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
8: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
9: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
10: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; cyclohexa-1,4-diene; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: glycosylation; ortho-esterification / 2: Deacetylation / 3: tritylation / 4: Acetylation / 5: Rearrangement / 6: Esterification / 7: Oxidation / 8: rhamnosylation / 9: Deacetylation / 10: Hydrogenolysis;
3,4-di(benzyloxy)phenethyl 3-O-allyl-β-D-glucopyranoside
253790-69-1

3,4-di(benzyloxy)phenethyl 3-O-allyl-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: 86 percent / pyridine / 0 - 20 °C
2: 92 percent / pyridine / 0 - 20 °C
3: 79 percent / AcOH / dioxane / 6 h / 110 °C
4: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
5: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
6: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
7: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
8: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; cyclohexa-1,4-diene; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: tritylation / 2: Acetylation / 3: Rearrangement / 4: Esterification / 5: Oxidation / 6: rhamnosylation / 7: Deacetylation / 8: Hydrogenolysis;
3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-β-D-glucopyranoside
253790-72-6

3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
3: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
4: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
5: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With dmap; selenium(IV) oxide; cyclohexa-1,4-diene; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Oxidation / 3: rhamnosylation / 4: Deacetylation / 5: Hydrogenolysis;
3,4-di(benzyloxy)phenethyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
253790-68-0

3,4-di(benzyloxy)phenethyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1: 94 percent / sodium methoxide / methanol / 2 h / 20 °C
2: 86 percent / pyridine / 0 - 20 °C
3: 92 percent / pyridine / 0 - 20 °C
4: 79 percent / AcOH / dioxane / 6 h / 110 °C
5: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
6: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
7: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
8: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
9: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; cyclohexa-1,4-diene; boron trifluoride diethyl etherate; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: tritylation / 3: Acetylation / 4: Rearrangement / 5: Esterification / 6: Oxidation / 7: rhamnosylation / 8: Deacetylation / 9: Hydrogenolysis;
3,4-di(benzyloxy)phenethyl 3-O-allyl-6-O-trityl-β-D-glucopyranoside
253790-70-4

3,4-di(benzyloxy)phenethyl 3-O-allyl-6-O-trityl-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 92 percent / pyridine / 0 - 20 °C
2: 79 percent / AcOH / dioxane / 6 h / 110 °C
3: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating
4: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C
5: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C
6: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C
7: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C
With pyridine; dmap; selenium(IV) oxide; cyclohexa-1,4-diene; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Acetylation / 2: Rearrangement / 3: Esterification / 4: Oxidation / 5: rhamnosylation / 6: Deacetylation / 7: Hydrogenolysis;

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