88642-46-0

Basic information

• Product Name: [(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]β-D-glucopyranoside
• Synonyms: (2R)-N-[(1S,2R,3E,7E)-1-(β-D-Glucopyranosyloxymethyl)-2-hydroxy-8-methyl-3,7-heptadecadienyl]-2-hydroxyhexadecanamide;(R)-N-[(1S,2R,3E,7E)-1-[(β-D-Glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadienyl]-2-hydroxyhexadecanamide;[(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]β-D-glucopyranoside;Cerebroside B;N-(2-Hydroxyhexadecanoyl)-1-(β-D-glucopyranosyloxy)-9-methyl-4,8-sphingadienine
• CAS NO: 88642-46-0
• Molecular Formula: C41H77NO9
• Molecular Weight: 728.05
• Mol File: 88642-46-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]β-D-glucopyranoside(88642-46-0)
• EPA Substance Registry System: [(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]β-D-glucopyranoside(88642-46-0)

Safety Data

• Hazardous Substances Data: 88642-46-0(Hazardous Substances Data)

Usage

Uses

Used in Photosynthesis:
MGDG is used as a structural component in the thylakoid membranes of chloroplasts for maintaining the fluidity and stability of the membrane, which is essential for the efficient functioning of photosynthesis.
Used in Health and Nutrition:
MGDG is studied for its potential health benefits, such as its antioxidant properties, which may help protect cells from damage caused by free radicals, and its anti-inflammatory properties, which could contribute to reducing inflammation in the body.
Used in Pharmaceutical and Nutraceutical Industries:
Given its potential health benefits, MGDG could be utilized in the development of pharmaceutical and nutraceutical products aimed at promoting health and well-being through its antioxidant and anti-inflammatory actions.
Used in Agricultural Research:
Understanding the role of MGDG in plant cell membranes can aid in agricultural research, potentially leading to the development of crops with improved photosynthetic efficiency and stress resistance.

Upstream product

• 16452-51-0 (R)-(-)-2-hydroxyhexadecanoic acid 
• 16742-51-1 methyl (R)-2-hydroxyhexadecanoate 
• 1220969-59-4 1-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-((benzoyloxy)hexadecanoyl)amino]-3-O-benzoyl-9-methyl-4,8-octadecadiene-1,3-diol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 100924-04-7 (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine 
• 100933-62-8 1-O-benzoylsphingadienine*HCl 
• 100924-01-4 (2'E,6'E,4S,1'R)-4-(1'-hydroxy-7'-methyl-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazolin-2-ene 
• 100933-63-9 (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine 
• 100924-05-8 (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine 
• 100924-06-9 (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine 
• 100923-97-5 (E)-1,1-dibromo-6-methyl-1,5-pentadecadiene 
• 100923-96-4 (E)-5-methyl-4-tetradecenal 
• 100923-95-3 (E)-5-methyl-4-tetradecenenitrile 
• 100923-94-2 (E)-1-bromo-4-methyl-3-tridecene 

Downstream Products

• 16452-51-0 (R)-(-)-2-hydroxyhexadecanoic acid 
• 76918-58-6 (R)-2-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexadecanoic acid methyl ester 
• 16742-51-1 methyl (R)-2-hydroxyhexadecanoate 

Relevant articles and documents

Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements

(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(i)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cereb

Efficient stereocontrolled synthesis of sphingadienine derivatives

Sphinga-4,8-dienines, principal long-chain bases of glycolipids in plants and fungi, were efficiently synthesized from l-serine. Hydrozirconation of pentadec-5-en-1-ynes followed by ZnBr2-catalyzed addition to Garner's aldehyde afforded protected sphinga-4,8-dienines stereoselectively. The (2S,3R,4E,8E)-9-methyl-sphingadienine derivative was then coupled with 2(R)-acetoxypalmitic acid derivative prepared via asymmetric dihydroxylation to give a protected ceramide, which was converted into the corresponding glucocerebroside in two steps.

SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-1-O-β-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE, THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE

The title compound was synthesized by employing (R)-2-aminohexadecanoic acid, D-glucose and (S)-serine as the chiral sources, and the synthetic sample was found to be chemically and biologically identical with the fruiting-inducing cerebroside isolated fr