Cuniloside B

Base Information

• Chemical Name: Cuniloside B
• CAS No.: 1187303-40-7
• Molecular Formula: C₂₆H₄₀O₁₀
• Molecular Weight: 512.598
• Mol file: 1187303-40-7.mol

Synonyms:Cuniloside B

Chemical Property of Cuniloside B

Chemical Property:

• PSA: 162.98000
• LogP: 0.87520

Purity/Quality:

98%min ^*data from raw suppliers

CunilosideB ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Cuniloside B is a monoterpenoid ester widely distributed across various Eucalyptus species, where it likely plays a role in essential oil biosynthesis or mobilization. Its synthesis involves glycosylation and acylation processes, utilizing compounds such as D-glucopyranose and (+)-(R)-oleuropeic acid. Analytical techniques, including LC-ESIMS and NMR, confirm its ubiquitous presence in eucalypt leaves, highlighting its significance in the genus.

Technology Process of Cuniloside B

There total 1 articles about Cuniloside B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 7.2%

D-glucose (50-99-7) + (+)-(R)-oleuropeic acid (22155-73-3) → 1,6-di-O-[(R)-oleuropeyl]-β-D-glucopyranose (1187303-40-7)

Guidance literature:

With 4-methyl-morpholine; dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 50 ℃; for 60h; Inert atmosphere;

DOI:10.1016/j.carres.2010.07.029

Reference yield:

1,6-di-O-[(R)-oleuropeyl]-β-D-glucopyranose (1187303-40-7) → (+)-(R)-oleuropeic acid (22155-73-3) + eucalmaidin A

Guidance literature:

With water; β-glucosidase; at 37 ℃; for 192h; Enzymatic reaction;

DOI:10.1021/np900290s

Reference yield:

1,6-di-O-[(R)-oleuropeyl]-β-D-glucopyranose (1187303-40-7) + sodium methylate (124-41-4) → (R)-methyl oleuropeic acid methyl ester

Guidance literature:

With methanol; for 2h;

DOI:10.1016/j.phytochem.2009.06.004

upstream raw materials:

D-glucose

(+)-(R)-oleuropeic acid

Downstream raw materials:

(+)-(R)-oleuropeic acid

Refernces

Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

10.1016/j.carres.2010.07.029

The research primarily focuses on the synthesis and widespread occurrence of monoterpenoid esters, cuniloside B and cypellocarpin C, in the Eucalyptus genus. Experiments involved the synthesis of these esters along with related natural products using reactants such as D-glucopyranose, (+)-(R)-oleuropeic acid, noreugenin, and various glycosides. The synthesis processes were optimized using different conditions and reagents, including phase transfer glycosylation, deacetylation with sodium methoxide, and acylation using HBTU–NMM–DMAP. The experiments also encompassed the extraction and analysis of leaf samples from 28 diverse eucalypt species, utilizing techniques like LC-ESIMS, NMR, and IR spectroscopy for compound identification and quantification. The study revealed that cuniloside B is present in all examined species, while cypellocarpin C is found in most, suggesting their potential roles in essential oil biosynthesis or mobilization.