20230-73-3

Basic information

• Product Name: 3-C-(hydroxymethyl)-β-D-erythrofuranose
• CAS NO: 20230-73-3
• Molecular Weight: 150.131
• Mol File: 20230-73-3.mol
• Article Data: 69

Chemical Properties

• CAS DataBase Reference: 3-C-(hydroxymethyl)-β-D-erythrofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-C-(hydroxymethyl)-β-D-erythrofuranose(20230-73-3)
• EPA Substance Registry System: 3-C-(hydroxymethyl)-β-D-erythrofuranose(20230-73-3)

Safety Data

• Hazardous Substances Data: 20230-73-3(Hazardous Substances Data)

Upstream product

• 153-18-4 rutin 
• 26544-34-3 apiin 
• 126054-82-8 atractyloside F 
• 126054-81-7 atractyloside E 
• 64481-62-5 methyl D-apiofuranoside 
• 58809-09-9 trillenoside A 
• 77658-50-5 deoxytrillenoside A 
• 104653-88-5 lariside 
• 107091-09-8 3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-<β-D-glucopyranosyl-(1->3)>-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside. 
• 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 

Downstream Products

• 6013-71-4 N-benzylphenylhydrazone of D-apiose 
• 10592-17-3 (3S)-2-hydroxymethylbutane-1,2,3,4-tetrol 

Relevant articles and documents

Chemical constituents of Miliusa balansae leaves and inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells

Abstract Methanolic extract of Miliusa balansae Finet et Gagnep exerts an anti-inflammatory effect via inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. Three new megastigmane glycosides, milbasides A-C (1-3), together with fifteen known compounds (4-18), were isolated from the active fraction. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, HR ESI MS, and CD analysis, as well as comparison with previously reported data. Compounds 1-3, 11 and 14 (20.0 μM) showed potent inhibitory activities with inhibition values of 98.5 ± 1.6%, 90.9 ± 7.8%, 84.8 ± 3.5%, 91.5 ± 8.7%, and 91.8 ± 2.7%, respectively. Our results suggest that megastigmane glycosides from M. balansae leaves may be used to treat inflammatory diseases.

Identification of compounds from the water soluble extract of cinnamomum cassia barks and their inhibitory effects against high-glucose-induced mesangial cells

The difficulty of diabetic nephropathy (DN) treatment makes prevention the best choice. Cinnamomum cassia barks, known as Chinese cinnamon or Chinese cassia, is one of the most popular natural spices and flavoring agents in many parts of the World. Since

Phenolic glycosides from sugar maple (Acer saccharum) bark

Four new phenolic glycosides, saccharumosides A-D (1-4), along with eight known phenolic glycosides, were isolated from the bark of sugar maple (Acer saccharum). The structures of 1-4 were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for cytotoxicity effects against human colon tumorigenic (HCT-116 and Caco-2) and nontumorigenic (CCD-18Co) cell lines.

Crotocascarins I-K: Crotofolane-type diterpenoids, crotocascarin γ, isocrotofolane glucoside and phenolic glycoside from the leaves of croton cascarilloides

From the 1-BuOH-soluble fraction of a methanol (MeOH) extract of the leaves of Croton cascarilloides, crotofolanes: crotocascarins I-K, nor-crotofolane: crotocascarin γ, isocrotofolane glucoside and phenolic glycoside were isolated by a combination of various separation techniques. Their structures were elucidated mainly from the NMR spectroscopic evidence. The structure of crotocascarin K was first elucidated by spectroscopic analysis and then was confirmed by X-ray crystallographic analysis. Its absolute structure was finally determined by the modified Mosher's method. Isocrotofolane glucoside was found to possess a new skeleton, however, its absolute structure remains to be determined.

Six new steroidal saponins from helleborus thibetanus

Six steroidal saponins, including five spirostanol glycosides, 1 - 5, and one furostanol glycoside 1- sulfonate, 6, previously unknown in nature, together with three known compounds, 7 - 9, were isolated from dried roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive 1D- And 2D-NMR experiments, along with IR and HR-ESI-MS data, as well as the results of acid hydrolysis. Compounds 1 - 5 possessed a C(25)=C(27) bond and were glycosylated at HO-C(1), which was unusual in steroidal saponins.

Acyl glycosides with rare β-d-apiofuranosyl-β-d-glucopyranosyl- β-d-apiofuranosyl from Erycibe hainanesis

Three new acyl glycosides with rare β-d-apiofuranosyl-(1 → 2)-[β-d-apiofuranosyl-(1 → 6)]-β-d-glucopyranosyl moieties, 2-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranosyl)-β-d-glucopyranosyl] -isopropyl alcohol (1), 1-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranos

Phenolic and iridoid glycosides from Strychnos axillaris

Five phenolic glycosides 1-5 and an iridoid glucoside 6 were isolated, together with 22 known compounds, from the dried barks and woods of Strychnos axillaris. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methodo

Two new C-glycosylflavones from Boea hygrometrica

Two new C-glycosylflavones, named 5,7,3′,4′-tetrahydroxy-6- methoxy-8-C-β-Dgluco-pyranosyl flavonoside (1), 5,3′,4′- trihydroxy-6,7-dimethoxy-8-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranosyl flavonoside (2), together with nine known compounds (3-11), were isolated from 50% acetone extract of Boea hygrometrica (Bunge.) R.Br. Their structures were established by spectroscopic techniques including MS, IR, UV, and 2D NMR.

A new phenolic glycoside from the barks of Cinnamomum cassia

A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhibition against ConA-induced T cells proliferation.

Five new phenolic glycosides from Hedyotis scandens

Five new phenolic glycosides, hedyotosides A-E (1-5), including a new cyanogenic glycoside (1), along with 10 known compounds (6-15) were isolated from the whole plants of Hedyotis scandens. The structures of compounds 1-5 were established by extensive spectroscopic analyses and acid hydrolysis. All the isolated compounds were evaluated for their in vitro antiviral activity against respiratory syncytial virus (RSV) with cytopathic effect (CPE) reduction assay. Compounds 6 and 15 showed anti-RSV effects with IC50 values of 20 and 25 μg/mL, respectively.

Chemical constituents from Saussurea cordifolia

Thirty-six naturally occurring compounds, including four C10-acetylenic glycosides and a lignan, were isolated from the whole plants of Saussurea cordifolia. Their structures were elucidated by means of spectroscopic and chemical methods to be 4,6-decadiyne-1-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (1), 4,6-decadiyne-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (2), (8E)-decaene-4, 6-diyn-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (3), (8Z)-decaene-4,6-diyn-1-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (4), and (2R, 3S, 4S)-4-(4-hydroxy-3-methoxybenzyl)-2-(5-hydroxy-3-methoxyphenyl)-3-(hydro xymethyl)-tetrahydrofuran-3-ol (5).

Two new lignan glycosides from the seeds of Cuscuta chinensis

Two new lignan glycosides, 2'-hydroxyl asarinin 2'-O-β-D- glucopyranoside (cuscutoside C, 1) and 2'-hydroxyl asarinin 2'-O-β-D- apiofuranosyl-(1→2)-[-D-glucopyranosyl-(1→6)]-D-glucopyranoside (cuscutoside D, 2), were isolated from the seeds of Cuscuta chinensis Lam., along with six known compounds, 2'-hydroxyl asarinin 2'-O-β-D- glucopyranosyl-(1→6)-D-glucopyranoside (3), 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1→2)-D-glucopyranoside (cuscutoside A, 4), kaempferol 3,7-di-O-β-D-glucopyranoside (5), 5-caffeoyl quinic acid (6), 4-caffeoyl quinic acid (7), and cinnamic acid (8). Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, ESI-MS/MS, 1H and 13C NMR, HSQC, HMBC, and TOCSY.

Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells in commemoration of Professor Xin-Sheng Yao's 80th Birthday

Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 μM, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 μM. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed.

A CHEMICAL STUDY OF PLANTS OF THE MONGOLIAN FLORA LARISIDE - A NEW SCOPOLETIN GLYCOSIDE FROM Salsola laricifolia

A new coumarin glycoside lariside - C21H26O13, mp 155-156 deg C (from methanol) - has been isolated from the epigeal part of Solsola laricifolia Turcz. et Litw.On the basis of acid hydrolysis and spectral characteristics the structure of lariside has been established as 7-2)-β-D-glucopyranosyloxy>-6-methoxy-2H-1-benzopyran-2-one.

Bufadienolides and ecdysteroids from the whole plants of Helleborus niger and their cytotoxicity

A new bufadienolide (1), two new bufadienolide glycosides (2 and 3), a new ecdysteroid (4), and four known compounds (5–8), were isolated from the whole plants of Helleborus niger L. (Ranunculaceae). The structures of the new compounds (1–4) were determined by spectroscopic analysis, including 2D NMR spectral data, and hydrolytic studies. Compounds 1–6 showed cytotoxicity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human small-cell lung cancer cells, with IC50 values ranging from 0.0055 to 1.9?μM. HL-60 cells treated with either 3 or 4 showed apoptosis characteristics, such as nuclear chromatin condensation, accumulation of sub-G1 cells, and activation of caspase-3/7.

Triterpenic saponins from Medicago marina L

The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.