28161-52-6

Basic information

• Product Name: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• Synonyms: beta-D-Fucose;(2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• CAS NO: 28161-52-6
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Mol File: 28161-52-6.mol

Chemical Properties

• Boiling Point: 323.9°Cat760mmHg
• Flash Point: 149.7°C
• Appearance: /
• Density: 1.556g/cm³
• PKA: 12.28±0.70(Predicted)
• CAS DataBase Reference: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(28161-52-6)
• EPA Substance Registry System: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(28161-52-6)

Safety Data

• Hazardous Substances Data: 28161-52-6(Hazardous Substances Data)

Upstream product

• 1028100-33-5 3-O-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1226-39-7 p-nitrophenyl-β-D-fucopyranoside 
• 1668-08-2 L-galactono-1,4-lactone 
• 24286-28-0 (3S,4S,5R)-dihydro-3,4-dihydroxy-5-((1'S)-1'-hydroxyethyl)furan-2(3H)-one 
• 1372946-80-9 methyl 6-bromo-6-deoxy-L-galactonate 
• 74032-91-0 p-nitrophenyl α-D-fucopyranoside 
• 1207550-40-0 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->4)-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 1207550-42-2 3-O-β-D-galactopyranosyl-(1->3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 6130-58-1 kaempferol-3-rutinoside 

Downstream Products

• 80483-13-2 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide 
• 127061-11-4 phenyl 1-thio-α/β-L-fucopyranoside 
• 153658-86-7 (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 135266-93-2 1,2,3,4-tetra-O-benzoyl-α-L-fucopyranoside 
• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 87908-23-4 2-methoxyethyl 2,3,4-tri-O-benzyl-β-L-fucopyranoside 
• 127874-85-5 2-methoxyethyl 2-O-benzyl-β-L-fucopyranoside 
• 127874-96-8 2-methoxyethyl 4-O-allyl-2-O-benzyl-β-L-fucopyranoside 
• 127874-86-6 2-methoxyethyl 2,4-di-O-benzyl-β-L-fucopyranoside 
• 127874-87-7 2-methoxyethyl 2,3-di-O-benzyl-β-L-fucopyranoside 
• 127880-29-9 2-methoxyethyl 2-O-allyl-3,4-di-O-benzyl-β-L-fucopyranoside 
• 127874-90-2 2-methoxyethyl 3-O-allyl-2,4-di-O-benzyl-β-L-fucopyranoside 
• 127874-94-6 2-methoxyethyl 4-O-allyl-2,3-di-O-benzyl-β-L-fucopyranoside 
• 127874-88-8 2-methoxyethyl 3-O-acetyl-2,4-di-O-benzyl-β-L-fucopyranoside 

Relevant articles and documents

Presenegenin glycosides from securidaca welwitschii

The five new presenegenin glycosides 1-5 were isolated from Securidaca welwitschii, together with one known sucrose diester. Compounds 1-4 were obtained as pairs of inseparable (E)/(Z)-isomers of a 3,4-dimethoxycinnamoyl derivative, i.e., 1/2 and 3/4. Their structures were elucidated mainly by 2D-NMR techniques and mass spectrometry as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D- glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1→4)-O-β- D-xylopyranosyl-(1→4)-O-3-O-acetyl-α-L-rhamnopyranosyl-(1→2) -O-[β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, and 3-O-(β-D-glucopyranosyl)presenegenin 28-[O-β-D-galactopyranosyl- (1→3)-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosyl] ester (5) (presenegenin=(2β,3β, 4α)-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid). Copyright 2010 Verlag Helvetica Chimica Acta AG, Zuerich, Switzerland.

New triterpenoid saponins from the aerial parts of Comastoma pedunculatum

Three new saikosaponin analogs, comastomasaponins I-K (1-3), were isolated from the aerial portions of Comastomapedunculatum. The structures of these compounds were elucidated on the basis of spectroscopic data analysis, and their nitric oxide production inhibitory activity was evaluated invitro.

STEROIDS OF THE FUROSTAN AND SPIROSTAN SERIES FROM Nolina microcarpa II. STRUCTURES OF NOLINOSPIROSIDE D AND NOLINOFUROSIDES D, E, AND F

Proofs are given of the structures of two new glycosides of the furostan series isolated from the leaves of the plant Nolina microcarpa S.Wats. (family Dracaenaceae).Nolinofuroside D is (25S)-furost-5-ene-1β, 3β,22 α,26-tetraol 1-O-β-D-galactopyranoside 26-O-β-D-glucopyranoside (I), and nolinofuranoside F is (25S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside 3-O-α-L-rhamnopyranoside (VII).The latter was characterized as its 22-O-methyl ether (VIII).Nolinofuranoside E (IV) has the structure of (25S)-furost-5-ene-1β,3β,22α,26-tetraol 26-O-β-glucopyranoside 1-O- 2)-β-D-fucopyranoside>, which followed from the structure of the fermentation product (VI).The products of the fermentation of the above-named compounds were present in the plant in only trace amounts.Only one of them - nolinospiroside D (III) - has not been described previously.This monoside of the spirostan series is (25S)-spirost-5-ene-1β,3β-diol 1-O-β-D-galactopyranoside.

New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight

As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s

Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities

Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r

Bioactive oleanane-type saponins from Hylomecon Japonica

Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.

Triterpene saponins from Silene gallica collected in North-Eastern Algeria

Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1–11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-D-glucuronic acid or β-D-galactopyranosyl-(1 → 3)-β-D-glucuronopyranoside and at C-28 by a β-D-fucopyranose substituted at C-2 by a β-D-glucose and at C-3 by a β-D-glucose or a β-D-quinovose.

Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities

A new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 - 3)-β-D-xylopyranosyl-(1 - 4)-α-L-rhamnopyranosyl-(1 - 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of Polygala arillata. The 11 known compounds were identified as oleanolic acid (2), 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3), trans-ferulic acid (4), trans-feruloyl-glucoside (5), feruloyl-glucoside (6), 2,4,6-trimethoxy-1-O-β-D-glycoside (7), 3-methoxy-4-hydroxybenzoic acid (8), monopentadecanoin (9), sinapic acid (10), p-hydroxybenzaldehyde (11), and palmitic acid (12). Among them, seven isolated compounds 1, 2, 4, 5, 7, 8, and 10 exhibited little cytotoxic activity on macrophage RAW 264.7 cells. Then, the inhibitory effects of 7 isolates on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were evaluated. As a result, 3 compounds have significant anti-inflammatory activity, and they were arillatanoside E (1), oleanolic acid (2), and 2,4,6-trimethoxy-1-O-β-D-glycoside (7).

Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera

Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark. The structures of 1-3 were determined by use of NMR spectra, HRESIMS, and chemical methods. Compounds 1-5 exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines (IC50 0.28-1.8 μM). Additionally, the apoptosis-inducing activity of compound 2 was evaluated by Hoechst 33342 staining and flow cytometry, while the effects of 2 on the activation of caspases-9, -8, and -3 in HL60 cells were revealed by Western blot analysis.

A new steroidal saponin from the tubers of ophiopogon japonicus and its protective effect against cisplatin-induced renal cell toxicity

A new furostanol saponin, ophiopogonin T, was isolated from the tubers of Ophiopogon japonicus. Its structure was established by extensive spectroscopic techniques including 1D (1 H and 13C) and 2D nuclear magnetic resonance (NMR) experiments (correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) and nuclear Overhauser effect spectroscopy (NOESY)), high-resolution electrospray ionization mass spectrometry (ESIMS), and chemical methods. Using cell-based assays, this compound was evaluated for its cytotoxic effect on cancer cell lines and its protective effect against anticancer drug-induced nephrotoxicity. Cisplatin-induced cytotoxicity in porcine kidney (LLC-PK1) cells was significantly reduced upon treatment with ophiopogonin T, without affecting human hepatoma (HepG2) cancer cell proliferation or tube formation in human umbilical vein endothelial cells (HUVECs). These results collectively reflect the beneficial effect of ophiopogonin T on the side effects of cisplatin.