10592-17-3

Basic information

• Product Name: 3-(hydroxymethyl)erythritol
• Synonyms: 3-(hydroxymethyl)erythritol
• CAS NO: 10592-17-3
• Molecular Formula: C₅H₁₂O₅
• Molecular Weight: 152.1458
• Mol File: 10592-17-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 467.2°Cat760mmHg
• Flash Point: 247.2°C
• Appearance: /
• Density: 1.536g/cm³
• Vapor Pressure: 2.38E-07mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 3-(hydroxymethyl)erythritol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(hydroxymethyl)erythritol(10592-17-3)
• EPA Substance Registry System: 3-(hydroxymethyl)erythritol(10592-17-3)

Safety Data

• Hazardous Substances Data: 10592-17-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H12O4/c6-1-4(2-7)5(9)3-8/h4-9H,1-3H2

Upstream product

• 1339943-03-1 [(5S)-2-phenyl-1,3-dioxolane-4,4,5-triyl]trimethanol 
• 25904-06-7 1,2:3,5-di-O-isopropylidene-α-D-threo-apiofuranose 
• 70147-50-1 3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside 
• 93836-28-3 3-C-(hydroxymethyl)-2,3-O-isopropylidene-erythritol 
• 30738-01-3 D-apiose 
• 639-97-4 D-apiose 

Downstream Products

• 1339943-10-0 (3S)-2,3-dihydroxy-2-[3,4,5-tris(benzyloxy)benzoyloxymethyl]butane-1,4-diyl bis[3,4,5-tris(benzyloxy)benzoate] 
• 1339943-12-2 (3S)-2-hydroxy-2-(benzoyloxymethyl)butane-1,3,4-triyl trisbenzoate 
• 93836-31-8 1,2,3,4-tetra-O-benzoyl-3-C-(benzoyloxymethyl)erythritol 
• 128554-57-4 apiitol 1,2,4,4'-tetraacetate 
• 128536-85-6 3-O-(methylthiomethyl)apiitol tetraacetate 
• 85373-03-1 apiitol 1,2,3,4,4'-pentaacetate 

Relevant articles and documents

New hemiterpenoid pentol and monoterpenoid glycoside of Torillis japonica fruit, and consideration of the origin of apiose

From the water-soluble portion of Torillis japonica D.C. fruit, a new hemiterpenoid pentol, (3R)-2-hydroxymethylbutane-1,2,3,4-tetrol (1) and a new monoterpenoid apiosyl-glucoside (4) have been isolated together with known (2S,3R)-2-methylbutane-1,2,3,4-tetrol (2) and hemiterpenoid glucoside (3). As 2 is a commonly existing constituent in Umbelliferous plants, and considered to be the first putative precursor of isoprenoid derived from glucose, we assumed that apiose and these hemiterpenoids may be biosynthesized from glucose by a mevalonate-independent route of isoprenoid.

An HIV RNase H inhibitory 1,3,4,5-tetragalloylapiitol from the African plant Hylodendron gabunensis

A new compound, 1,3,4,5-tetragalloylapiitol (1), was isolated from the aqueous extract of the plant Hylodendron gabunensis and was found to be a potent inhibitor of RNase H enzymatic activity. The structure of 1 was elucidated by NMR analyses to be an apiitol (2) sugar moiety substituted with four gallic acid residues. Optical rotation measurements of the free sugar following basic hydrolysis indicated that the 35 absolute configuration was the same as that of D-apiitol. Compound 1 inhibited HIV-1, HIV-2, and human RNase H with IC 50 values of 0.24, 0.13, and 1.5 μM, respectively, but it did not show inhibition of E. coli RNase H at 10 μM.

Synthesis of 3-C-(hydroxymethyl)erythritol and 3-C-methylerythritol.

3-C-(Hydroxymethyl)erythritol was prepared from 3-C-(hydroxymethyl)-2,3-O-isopropylidene-D-erythro-tetrofuranose (4) by hydrolysis followed by reduction, or by reduction followed by hydrolysis. Monotosylation of 4, followed by reduction with lithium aluminum hydride and hydrolysis, afforded 3-C-methylerythritol.