51771-52-9

Basic information

• Product Name: SIMMONDSIN
• Synonyms: SIMMONDSIN;(1z,2-alpha,3-beta,4-beta,6-beta)-ene);2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexylbeta-d-glucoside;acetonitrile,(6-(beta-d-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylid;[(1Z,2α,3β,4β,6β)-6-(β-D-Glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene]acetonitrile;Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)-;Acetonitrile, (6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (1Z,2-alpha,3-beta,4-beta,6-beta)-
• CAS NO: 51771-52-9
• Molecular Formula: C₁₆H₂₅NO₉
• Molecular Weight: 375.37
• Mol File: 51771-52-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 95～100℃
• Boiling Point: 637.5°Cat760mmHg
• Flash Point: 339.4°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 6.16E-19mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: SIMMONDSIN(CAS DataBase Reference)
• NIST Chemistry Reference: SIMMONDSIN(51771-52-9)
• EPA Substance Registry System: SIMMONDSIN(51771-52-9)

Safety Data

• Hazardous Substances Data: 51771-52-9(Hazardous Substances Data)

Usage

Description

SIMMONDSIN, also known as simmondsin, is a bioactive compound derived from the Jojoba plant (Simmondsia chinensis). It is found in jojoba meal and has been demonstrated to possess various beneficial properties, particularly in the context of appetite regulation and weight management.

Uses

Used in Pharmaceutical Applications:
SIMMONDSIN is used as an appetite suppressant for promoting weight management and reducing food intake in adult rats. Its ability to decrease food consumption makes it a potential candidate for the development of pharmaceuticals aimed at addressing obesity and related health issues.
Used in Nutritional and Dietary Supplements:
In the nutritional and dietary supplement industry, SIMMONDSIN is used as an ingredient to help individuals control their appetite and support weight loss efforts. Its inclusion in these products can contribute to a healthier lifestyle by assisting in the management of caloric intake and promoting overall well-being.
Used in Food and Beverage Industry:
SIMMONDSIN may also find applications in the food and beverage industry as a natural additive to help reduce the overall caloric content of certain products. By incorporating simmondsin into the formulation of snacks, beverages, or other consumables, manufacturers can offer healthier options to consumers seeking to manage their weight or maintain a balanced diet.

InChI:InChI=1/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10-,11+,12-,13+,14-,15+,16-/m1/s1

Upstream product

• 135131-70-3 (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane 
• 51385-17-2 simmondsin penta-O-acetate 
• 58769-23-6 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol 
• 135131-63-4 1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol 
• 142543-92-8 1L-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol 
• 19647-44-0 1L-1,2:3,4-di-O-isopropylidene-5,6-di-O-methyl-chiro-inositol 
• 142543-94-0 1D-(1,2,5/3,4)-5-O-(p-methoxybenzyl)-1,2-di-O-methylcyclohexanepentaol 
• 135131-64-5 1D-(1,2,5/3,4)-3,4-O-isopropylidene-5-O-(p-methoxybenzyl)-1,2-di-O-methylcyclohexanepentaol 
• 142543-96-2 (2Z)-(1R,3S,4S,5S)-2-cyanomethylene-3-hydroxy-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane 
• 135131-66-7 1D-(1,2,5/3,4)-5-O-(p-methoxybenzyl)-1,2-di-O-methyl-3-O-(tetrahydropyran-2-yl)cyclohexanepentaol 
• 135131-67-8 2D-(2/3,4,6)-6-O-(p-methoxybenzyl)-3,4-di-O-methyl-2-O-(tetrahydropyran-2-yl)-2,3,4,6-tetrahydroxycyclohexanone 
• 135131-69-0 (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane 
• 135131-65-6 1D-(1,2,5/3,4)-4-O-benzoyl-5-O-(p-methoxybenzyl)-1,2-di-O-methylcyclohexanepentaol 
• 135131-62-3 1L-3-O-benzoyl-1,2-O-isopropylidene-5,6-di-O-methyl-4-O-methylsulfonyl-chiro-inositol 

Downstream Products

• 42973-56-8 2-(2-hydroxy-3-methoxyphenyl)acetonitrile 

Relevant articles and documents

Synthesis and Absolute Configuration of the Naturally Occurring Cyano Glucoside Simmondsin

The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported.An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, follwed by deprotection to provid