6696-41-9

Basic information

• Product Name: 6-DEOXY-L-GALACTOPYRANOSE
• Synonyms: 6-DEOXY-L-GALACTOPYRANOSE;6-DEOXY-L-GALACTOSE;6-DEOXY-ALPHA-L-GALACTOSE;3,4,5-TRIS-BENZYLOXY-2-METHYL-6-P-TOLYLSULFANYL-TETRAHYDRO-PYRAN;L-FUC;L-(-)-FUCOSE;L-FUCOSE;L-(-)-Fucose,97%
• CAS NO: 6696-41-9
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• EINECS: 219-452-7
• Mol File: 6696-41-9.mol

Chemical Properties

• Melting Point: 136-140°C
• Boiling Point: 323.9°C at 760 mmHg
• Flash Point: 149.7°C
• Appearance: /
• Density: 1.556g/cm³
• Vapor Pressure: 1.99E-05mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Store at RT.
• Sensitive: Hygroscopic
• Merck: 14,4279
• BRN: 1422661
• CAS DataBase Reference: 6-DEOXY-L-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-DEOXY-L-GALACTOPYRANOSE(6696-41-9)
• EPA Substance Registry System: 6-DEOXY-L-GALACTOPYRANOSE(6696-41-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• Hazardous Substances Data: 6696-41-9(Hazardous Substances Data)

Usage

Definition

ChEBI: An L-fucopyranose having alpha-configuration at the anomeric centre.

InChI:InChI=1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6-/m0/s1

Upstream product

• 67-56-1 methanol 
• 1099684-82-8 p-cyanophenyl α-L-fucopyranoside 
• 10231-84-2 (4-nitro-phenyl)-α-L-fucopyranoside 
• 157843-41-9 2-chloro-4-nitrophenyl α-L-fucopyranoside 
• 88434-20-2 6α-O-[β-D-galactopyranosyl-(1→3)-β-D-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-xylopyranosyl-(1→3)-β-D-quinovopyranosyl]-20-hydroxy-23-one-5α-cholest-9(11)-en-3β-yl sodium sulfate 
• 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. 
• 74032-91-0 p-nitrophenyl α-D-fucopyranoside 
• 865688-88-6 quercitrin 
• 6130-58-1 kaempferol-3-rutinoside 
• 55466-05-2 Zizyphus saponin III 
• 77174-32-4 Zizyphus saponin I 
• 1033607-50-9 chrysin 4'-O-α-D-6-deoxyallopyranoside 

Downstream Products

• 53829-55-3 α-L-Furopyranose 1,2 : 3,4-bis(butanboronat) 
• 76222-16-7 3-O-α-L-fucopyranosyl-D-glucose 
• 263008-59-9 β-L-fucopyranosylnitromethane 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 103419-79-0 α-L-fucopyranosylamine 
• 153658-86-7 (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 65310-00-1 (3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 57472-03-4 methyl β-L-fucofuranoside 
• 57472-02-3 methyl α-L-fucofuranoside 
• 14687-15-1 methyl L-fucopyranoside 
• 1128-40-1 methyl β-L-fucopyranoside 
• 5328-43-8 1-deoxy-L-galactitol 
• 196397-58-7 phenyl 3,4-O-isopropylidene-1-thio-α-L-fucopyranoside 
• 196397-59-8 phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 

Relevant articles and documents

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

Electrochemical detection of fucosidase activity in human serum

Liver cancer is one of the most common malignant tumors globally and is the second leading cause of cancer deaths in Taiwan. The activity of α-fucosidase (AFU) in the human body has been confirmed by many clinical studies and experiments to be applicable in the early diagnosis of primary liver cancer. Herein, an electrochemical method for determining AFU activity was developed based on measuring p-nitrophenol (pNP), which is a product of the reaction between AFU and p-nitrophenyl-α-L-fucopyranoside. The electrochemical detection of pNP in serum samples exhibited a wide linear range (2.5–250 μM), which corresponds to approximately 2.5–250 U/L AFU. The recovery of AFU measured upon enzyme addition to standard serum was 97–110%. Moreover, no potential interferants had a significant effect on pNP quantification. In contrast, an optical absorption method was subject to interference by the serum color. Further, the linear range for pNP was only 2.5–50 μM and the recovery of AFU was 165–219%. The performance of this absorption method could lead to a misjudgment of the disease course. Therefore, the electrochemical method for AFU activity determination has greater potential for use in clinical applications.

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

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.

Trifasciatosides A-J, steroidal saponins from Sansevieria trifasciata

Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1H-NMR, 13C-NMR, 1H-1H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells.

Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines

Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N–T (1–7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A–M (8–20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50?=?11.2, 14.3, and 6.9?μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.

Leptocarposide: A new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin-8-C-glucoside (2) and 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(R)-2-hydroxypalmitoylamino]-8- octadecen-1,3- diol (3) was isolated from the n-butanol-soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2-diphenyl-1-picrylhydrazyl and reveals non-potent antioxidant activities, while compound 2 shows SC50 of 0,038 mM.

METHOD FOR PRODUCING L-FUCOSE

Method for producing L-fucose includes in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid of a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursor as shown in Formula A, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.

METHOD FOR PRODUCING L-FUCOSE

The present invention provides: in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid or a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursoras shown in Formula A below, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.