84744-28-5

Basic information

• Product Name: calceolarioside A
• Synonyms: calceolarioside A;2-(3,4-Dihydroxyphenyl)ethyl 4-O-[(E)-3-(3,4-dihydroxyphenyl)propenoyl]-β-D-glucopyranoside;Desrhamnosyl acteoside
• CAS NO: 84744-28-5
• Molecular Formula: C₂₃H₂₆O₁₁
• Molecular Weight: 478.44594
• Mol File: 84744-28-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 784.7°C at 760 mmHg
• Flash Point: 269.8°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 6.18E-26mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: ?20°C
• PKA: 9.31±0.10(Predicted)
• CAS DataBase Reference: calceolarioside A(CAS DataBase Reference)
• NIST Chemistry Reference: calceolarioside A(84744-28-5)
• EPA Substance Registry System: calceolarioside A(84744-28-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 84744-28-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1

Upstream product

• 61276-17-3 Acteoside 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 604-69-3 β-D-glucose pentaacetate 
• 179128-84-8 (E)-3-(3,4-bis(allyloxy)phenyl)acrylic acid 
• 10597-60-1 hydroxytyrosol 
• 1600528-79-7 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl4-O-[3,4-bis-(O-tert-butyldimethylsilyl)-caffeoyl]-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside 
• 1600528-77-5 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl4-O-[3,4-bis-(O-tert-butyldimethylsilyl)-caffeoyl]-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside 
• 1600528-74-2 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside 
• 1600528-95-7 C₁₆H₂₂O₅S 
• 246872-15-1 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethanol 
• 1600528-75-3 p-tolyl 3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-thio-β-D-glucopyranoside 
• 104777-69-7 3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-O-α-rhamnopyranosyl-(1->6)-4-caffeoyl-β-D-glucopyranoside 
• 131903-54-3 Lavandulifolioside 

Relevant articles and documents

Short Synthesis of Phenylpropanoid Glycosides Calceolarioside A and Syringalide B

An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O -4 cinnamoylation of unprotected 2-phenylethyl-β- d -glucosides with cinnamic anhydrides using a chiral 4-pyrrolidinopyridine organocatalyst. This approach serves as a model for the short synthesis of phenylpropanoid glycosides acylated at O -4 without protection/deprotection steps.

A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides

A general strategy for the synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3 and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formyl morpholine modulated glycosylation methods for the construction of 1,2-trans β- and α-glycosidic bonds. The reported strategy does not invoke the use of the participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. A preliminary study of the anti-proliferation properties of the PhG compounds 1-4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation. This journal is the Partner Organisations 2014.

NINE PHENETHYL ALCOHOL GLYCOSIDES FROM STACHYS SIEBOLDII

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.