65982-27-6

Basic information

• Product Name: Epirhododendrin
• Synonyms: (S)-Rhododendrol 2-O-β-D-glucopyranoside;[(2S)-4-(4-Hydroxyphenyl)butane-2-yl]β-D-glucopyranoside;[(S)-1-Methyl-3-(4-hydroxyphenyl)propyl]β-D-glucopyranoside;[(S)-4-(4-Hydroxyphenyl)butan-2-yl]β-D-glucopyranoside;Epirhododendrin;epi-Rhododendrin
• CAS NO: 65982-27-6
• Molecular Formula: C₁₆H₂₄O₇
• Molecular Weight: 328.35756
• Mol File: 65982-27-6.mol

Chemical Properties

• Melting Point: 81-84 °C
• Boiling Point: 571.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• PKA: 10.08±0.15(Predicted)
• CAS DataBase Reference: Epirhododendrin(CAS DataBase Reference)
• NIST Chemistry Reference: Epirhododendrin(65982-27-6)
• EPA Substance Registry System: Epirhododendrin(65982-27-6)

Safety Data

• Hazardous Substances Data: 65982-27-6(Hazardous Substances Data)

Upstream product

• 152339-90-7 rhododendrin pentapivalate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 81058-26-6 1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose 
• 152339-89-4 epi-rhododendrin pentapivalate 
• 152339-87-2 (S)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 152339-92-9 (R)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 59092-94-3 (R)-rhododendrol 
• 152339-86-1 (S)-4-(4′-methoxyphenyl)-2-butanol 
• 39516-05-7 (R)-4-(4′-methoxyphenyl)-2-butanol 
• 59092-94-3 (+)-rhododendrol 
• 152339-88-3 (R)-4-(p-methoxyphenyl)butan-2-ol 3,5-dinitrobenzoate 

Downstream Products

• 92620-71-8 rhododendrin pentaacetate 
• 59092-94-3 (R)-rhododendrol 
• 59092-94-3 (+)-rhododendrol 

Relevant articles and documents

Chemical synthesis, redox transformation, and identification of sonnerphenolic C, an antioxidant in Acer nikoense

Sonnerphenolic C (3), which was predicted in a redox product of epirhododendrin (1) isolated from Acer nikoense, was synthesized for the first time via the epimeric separation of benzylidene acetal intermediates as a key step. From a similar synthetic route, 1 was obtained concisely. As a result of their antioxidative evaluation, only 3 revealed potent activity. The redox transformation of 1 into 3 was achieved in the presence of tyrosinase and vitamin C. Moreover, 3 was identified in the decoction of A. nikoense by HPLC analysis with the effective use of synthesized 3. Thus, a novel naturally occurring antioxidant 3 was developed through the sequential flow including redox prediction, chemical synthesis, evaluation of the activity, and identification as the natural product.

Synthesis of rhododendrin and epi-rhododendrin,

The first synthesis of rhododendrin 1 and epi-rhododendrin 2 was achieved by starting from ethyl (S)-3-hydroxybutanoate 4, p-bromoanisole and D-glucose.Rhododendrin 1 is known as the hepatoprotective constituent of Taxus baccata L. Keywords: betuligenol / betuloside / epi-rhododendrin / rhododendrin / rhododendrol