Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside

Base Information

• Chemical Name: Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
• CAS No.: 150995-11-2
• Molecular Formula: C21H36 O10
• Molecular Weight: 448.511
• DSSTox Substance ID: DTXSID001313997
• Nikkaji Number: J1.489.123D,J872.360E
• Wikidata: Q105111753
• Mol file: 150995-11-2.mol

Synonyms:geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside;geranyl 6-O-xylopyranosyl-glucopyranoside;GXPGP

Chemical Property of Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 9.03E-21mmHg at 25°C
• Boiling Point: 669.2°Cat760mmHg
• PKA: 12.88±0.70(Predicted)
• Flash Point: 358.5°C
• PSA: 158.30000
• Density: 1.33g/cm³
• LogP: -1.04110
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 448.23084734
• Heavy Atom Count: 31
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCOC1C(C(C(C(O1)COC2C(C(C(CO2)O)O)O)O)O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O)O)O)/C)C
• Use Description: Geranyl 6-O-xylopyranosyl-glucopyranoside is a natural compound found in various plants, and its applications span several fields. In the field of botany and plant biology, this compound plays a role in the biosynthesis of secondary metabolites and serves as a storage form of geranyl, which is essential for the production of various aromatic compounds. In the cosmetic and fragrance industry, it contributes to the formulation of perfumes and scented products due to its pleasant aroma. Furthermore, in traditional medicine, it has been explored for its potential health benefits, such as antioxidant properties and its role in herbal remedies. Its diverse uses highlight its significance in both the natural world and various human endeavors, from plant biology to cosmetics and wellness.

Technology Process of Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside

There total 14 articles about Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside 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: 71.0%

geranyl 2,3,4,2',3',4'-O-hexabenzoyl-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside (192827-14-8) → geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (150995-11-2,152520-94-0,197508-58-0)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 0.5h;

DOI:10.3987/COM-05-10640

Reference yield: 8.0%

Geraniol (106-24-1) + p-nitrophenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside → geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (150995-11-2,152520-94-0,197508-58-0)

Guidance literature:

With sodium acetate buffer; Penicillium multicolor IAM7153 β-primeverosidase; In water; at 40 ℃; for 3.5h; pH=5.5;

DOI:10.1080/07328300500439413

Reference yield:

Geraniol (106-24-1) → geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (150995-11-2,152520-94-0,197508-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Hg(CN)2 / acetonitrile / 3 h / Ambient temperature

2: NaOMe / methanol / 15 h / Ambient temperature

With sodium methylate; mercury(II) cyanide; In methanol; acetonitrile;

DOI:10.1021/jf960852b

upstream raw materials:

geranyl 2,3,4,2',3',4'-O-hexabenzoyl-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside

Geraniol

geranyl 6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

geranyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Downstream raw materials:

1-O-β-D-xylopyranosyl-(1,6)-β-D-glucopyranoside

Geraniol

Refernces

• 1、 Kawahara, Eiji,Fujii, Mikio,Ida, Yoshiteru,Akita, Hiroyuki. "Chemoenzymatic synthesis of naturally occurring geranyl 6-o-glycosyl-β-d-glucopyranosides". . p. 323 - 330. Retrieved 2007/10/03.
• 2、 Matsumura, Sachiko,Takahashi, Shunya,Nishikitani, Mariko,Kubota, Kikue,Kobayashi, Akio. "The Role of Diglycosides as Tea Aroma Precursors: Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves". . p. 2674 - 2678. Retrieved 2007/10/03.