117857-64-4

Basic information

• Product Name: O³-methyl-6-deoxy-L-idose
• Synonyms: O³-methyl-6-deoxy-L-idose
• CAS NO: 117857-64-4
• Molecular Weight: 178.185
• Mol File: 117857-64-4.mol

Chemical Properties

• CAS DataBase Reference: O³-methyl-6-deoxy-L-idose(CAS DataBase Reference)
• NIST Chemistry Reference: O³-methyl-6-deoxy-L-idose(117857-64-4)
• EPA Substance Registry System: O³-methyl-6-deoxy-L-idose(117857-64-4)

Safety Data

• Hazardous Substances Data: 117857-64-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 911649-24-6 methyl-(2,3-anhydro-6-deoxy-α-L-talopyranoside) 
• 124-41-4 sodium methylate 
• 54943-65-6 methyl 3,4-anhydro-6-deoxy-α-L-talopyranoside 
• 38791-27-4 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 15354-69-5 5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 
• 16714-09-3 3-O-methyl-5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 
• 1159579-91-5 hoodigoside W 
• 1159579-92-6 hoodigoside X 
• 1159579-93-7 calogenin 20-O-β-D-glucopyranosyl-3-O-β-D-thevetopyranosyl-(1->4)-β-D-oleandropyranoside 
• 1279102-01-0 C₃₁H₄₆O₁₀ 
• 1129992-63-7 3-O-β-D-glucopyranosyl-(1->4)-β-D-thevetopyranosyl-(1->4)-β-D-oleandropyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-digitoxopyranosyl-12-O-benzoyl-dihydrosarcostin 
• 1417887-96-7 stauntogenin B 3-O-α-L-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-thevetopyranoside 
• 1417887-93-4 stauntogenin 3-O-α-L-diginopyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-thevetopyranoside 

Downstream Products

• 112047-81-1 O³-methyl-L-xylo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 112047-81-1 O³-methyl-D-arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 112047-81-1 O³-methyl-D-ribo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 

Relevant articles and documents

Two new 14, 15-secopregnane-type steroidal glycosides from the roots of Cynanchum limprichtii

Two new steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digito

New C21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury

Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C21 steroidal glycosides (1–4) and one known compound stauntoside F (5). Their chemical structures were characterized by sophisticated analyses of IR, HR

Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: New procedure for separation of highly polar glycoside fractions and taxonomic revision

Five new triterpene glycosides, liouvillosides A1 (1), A 2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-1H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.

Melanogenesis inhibitory pregnane glycosides from Cynanchum atratum

Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1–3) along with four known compounds (4–7). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds 4–7 dose-dependently inhibited the melanin production with the IC50 values ranging from 4 μM to 33 μM.

New Sweet-Tasting C21-Pregnane Glycosides from Pericarps of Myriopteron extensum

Ten novel C21 pregnane glycosides, extensumside C-L (1-10), were isolated as highly sweet-tasting substances from the edible pericarps of Myriopteron extensum (Wight) K. Schum by sensory-guided fractionation and purification. Their structures were determined through 1D and 2D NMR, such as HSQC, HMBC, 1H-1H COSY, HSQC-TOCSY, and ROESY, as well as other spectroscopic analysis combined with chemical evidence. These compounds shared the same aglycone, 3β,16α-dihydroxy-pregn-5-en-20-one, and contained the deoxysugar chain and the glucose chain which were linked to C-3 and C-16 of the aglycone, respectively. The sweetness potency was evaluated by a human sensory panel test and preliminary structure-taste relationship was discussed. The sweetness intensities of these compounds are between 50 and 400 times greater than that of sucrose. Furthermore, quantitation analyses of compounds 1, 3, 4, and 6 in different parts of M. extensum indicated that the concentrations of these sweet components in the pericarps are obviously higher than those in stems and roots.

C21 steroidal glycosides from Cynanchum stauntonii induce apoptosis in HepG2 cells

Two new (1–2) and three known (3–5) C21 steroidal glycosides were isolated from Cynanchum stauntonii. Their structures were elucidated on the basis of 1D and 2D-NMR spectroscopic data as well as HRTOFMS analysis. The cytotoxicity of the compoun

New calogenin pregnane glycoside derivative from Huernia saudi- arabica and its Lipase and α-Glucosidase Inhibitory Activities

As ongoing investigation of Huernia saudi-arabica D.V.Field (Asclepiadaceae), a new steroidal pregnane glycoside (Huernioside A) was isolated from dichloromethane fraction (DCM); it was identified as 3β, 11, 14β, 20(R)-tetrahydroxy-pregna-5,9(11)-diene-3-O-β-D-thevetopyranosyl-(1-4)-β-D-cymaropyranoside(HCP) through analysis of 1D, 2D NMR besides ESI-MS data. The alcoholic extract of the aerial part (ALE), DCM and HCP showed inhibitory potential against pancreatic lipase compared to orilstat. Among the tested samples, the ALE and HCP exhibited a promising pancreatic lipase inhibitory commotion through IC50 values of 0.61 ± 0.15, 1.23 ± 0.07 mg/ml (equivalent to 88.8 μM), respectively. HCP was prevailed to have a mixed mode of inhibition as exposed by enzyme kinetic studies. Hydrophobic interactions were the major forces involved in ligand enzyme interactions. In contrast, moderate α-glucosidase inhibitory activities were evidenced for ALE and HCP (% inhibition: 24.8 ± 1.8 and 26.6 ± 2.5, respectively) compared to acarbose. This investigation is the first to report on the possible in vitro anti-obesity and anti-diabetic impact of H. saudi-arabica.

Four new pregnane glycosides from Gymnema latifolium and their α-glucosidase and α-amylase inhibitory activities

Four new pregnane glycosides, gymlatifosides A - D (1 ? 4) and one known pregnane glycoside, verticilloside J (5) were isolated from the leaves of Gymnema latifolium Wall. ex Wight. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, HR-ESI-MS, and in comparison with the reported data. All these compounds were tested for α-glucosidase and α-amylase inhibitory activities. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 37.8 ± 1.5% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 7.0 to 30.1%. In addition, all compounds 1–5 showed moderate/weak anti α-amylase activity in the investigated test.

Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Decne.) Schltr.ex Levl.

Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-d-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-β-d-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-β-d-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na+/K+-ATPase with IC 50 values of 21 and 29 μM, respectively, whereas ouabain as a positive control displayed an IC50 value of 3.5 μM.

Hirundigenin type C21 steroidal glycosides from Cynanchum stauntonii and their anti-inflammatory activity

Six new hirundigenin-type C21 steroidal glycosides, namely hirundigosides E-J (1-6), were obtained from the dried roots of Cynanchum stauntonii. Their chemical structures were elucidated by analyses of HR ESI-TOF MS, 1D, 2D-NMR, and X-ray cryst