4682-46-6

Basic information

• Product Name: MADUROSE
• Synonyms: MADUROSE;D-Galactose, 3-O-methyl-;3-O-Methyl-D-galactose
• CAS NO: 4682-46-6
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• Mol File: 4682-46-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 144-147 °C
• Boiling Point: 474.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.394±0.06 g/cm3(Predicted)
• PKA: 12.33±0.20(Predicted)
• CAS DataBase Reference: MADUROSE(CAS DataBase Reference)
• NIST Chemistry Reference: MADUROSE(4682-46-6)
• EPA Substance Registry System: MADUROSE(4682-46-6)

Safety Data

• Hazardous Substances Data: 4682-46-6(Hazardous Substances Data)

Usage

Uses

Madurose is an extracted chemical from mushroom that is used to treat melanoma cancer.

Synthetic route

methyl D-galactopyranoside (97-30-3, 617-04-9, 709-50-2, 1824-94-8, 2152-78-5, 3149-68-6, 3396-99-4, 6819-48-3, 18469-06-2, 20550-04-3, 22277-65-2, 29411-57-2, 35437-40-2, 35437-43-5, 36191-11-4, 36191-12-5, 39598-79-3, 39598-80-6, 39598-89-5, 51023-63-3, 51223-62-2, 51224-38-5, 51224-39-6, 51224-40-9, 51224-41-0, 51819-81-9, 51819-82-0, 51819-83-1, 56688-81-4, 62279-53-2, 64281-79-4, 64281-80-7, 64912-19-2, 66101-73-3, 78184-90-4, 84368-39-8, 84368-40-1, 84368-41-2, 92142-37-5, 93302-26-2, 103421-28-9, 115794-08-6) + methyl iodide (74-88-4) → 3-O-methyl-D-galactose (4682-46-6)

Conditions	Yield
With silver(l) oxide 1.) MeOH, 40 deg C, 150 min; Multistep reaction;

methyl iodide (74-88-4) + methyl- → 3-O-methyl-D-galactose (4682-46-6)

Conditions	Yield
With N,N-dimethyl-formamide; silver(l) oxide Erwaermen einer Loesung des Reaktionsprodukts in Aceton mit wss.Salzsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit wss.Salzsaeure;

methyl- → 3-O-methyl-D-galactose (4682-46-6)

Conditions	Yield
With sulfuric acid; acetone

methyl iodide (74-88-4) + methyl- → 3-O-methyl-D-galactose (4682-46-6)

Conditions	Yield
With N,N-dimethyl-formamide; silver(l) oxide Behandeln des Reaktionsprodukts mit Chlorwasserstoff enthaltendem Aethanol und Erhitzen des danach isolierten Reaktionsprodukts mit wss.Salzsaeure;

linear 3-O-methylated galactan WCCP-N-b from Cantharellus cibarius → D-Mannose (3458-28-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + 3-O-methyl-D-galactose (4682-46-6)

Conditions	Yield
With trifluoroacetic acid at 80℃; for 1h;

3-O-methyl-D-galactose (4682-46-6) + phenylhydrazine (100-63-0) → O3-methyl-D-lyxo-[2]hexosulose-bis-phenylhydrazone (51532-94-6)

3-O-methyl-D-galactose (4682-46-6) + ethanethiol (75-08-1) → O3-methyl-D-galactose diethyl dithioacetal (15354-65-1)

Conditions	Yield
With hydrogenchloride

3-O-methyl-D-galactose (4682-46-6) + acetone (67-64-1) → 1,2:5,6-di-O-isopropylidene-3-O-methyl-α-D-galactofuranose (32087-37-9)

Conditions	Yield
With sulfuric acid; ethyl acetate for 2h;

3-O-methyl-D-galactose (4682-46-6) + water (7732-18-5) + potassium acetate (127-08-2) + lead(IV) tetraacetate (546-67-8) + acetic acid (64-19-7) → formic acid (64-18-6)

Conditions	Yield
at 27℃; Zeitlicher Verlauf;

3-O-methyl-D-galactose (4682-46-6) → 2,4,5,6-Tetra-O-acetyl-3-O-methyl-D-galactose-diaethyl-dithioacetal (15354-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl 2: Py View Scheme

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 71072-42-9 3-O-Methyl-D-glucal 
• 43138-64-3 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 1220913-35-8 3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-Dglucopyranosyl]-4-O-[3-O-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-9(11),25(26)-dien-16-one 
• 1220913-36-9 3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-7(8),25(26)-dien-16-one 
• 97-30-3 methyl D-galactopyranoside 
• 74-88-4 methyl iodide 

Downstream Products

• 1518-59-8 D-arabino-3-deoxy-hexonic acid 
• 498-43-1 3-deoxy-D-ribo-hexonic acid 
• 533-67-5 2-Deoxy-D-ribose 
• 55651-99-5 O⁴,O⁶-((R)-benzylidene)-O³-methyl-D-glucose 
• 93302-38-6 (2R,4aR,6S,7R,8R,8aR)-6,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol 
• 70144-57-9 methyl 4,6-O-benzylidene-3-O-methyl-β-D-glucopyranoside 
• 111210-92-5 p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside 
• 2887-05-0 O¹,O²,O⁴,O⁶-Tetrabenzoyl-O³-methyl-β-D-glucopyranose 
• 36256-85-6 3-O-methyl-Δ-fructose 
• 3254-27-1 O²,O⁴;O⁵,O⁶-((S,R)-dibenzylidene)-O³-methyl-D-glucitol 
• 3254-27-1 O²,O⁴;O⁵,O⁶-((S,S)-dibenzylidene)-O³-methyl-D-glucitol 
• 1333966-04-3 C₁₉H₂₀B₂O₆ 
• 1333966-00-9 C₁₃H₁₇BO₆ 
• 1333965-99-3 C₁₃H₁₇BO₆ 

Relevant articles and documents

A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities

Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.

Pseudocnoside A, a new cytotoxic and antiproliferative triterpene glycoside from the sea cucumber Pseudocnus dubiosus leoninus

A new triterpene glycoside, pseudocnoside A (1), was isolated from the sea cucumber Pseudocnus dubiosus leoninus. The structure of the new compound was established on the basis of extensive NMR spectroscopic analysis (1H and 13C NMR, 1H,1H-COSY, HMBC, HSQC, TOCSY and NOESY), HR-ESI-MS data and chemical transformations. In addition, the cytotoxicity and antiproliferative activities of 1 and structurally related triterpene glycosides isolated from the sea cucumbers Psolus patagonicus and Hemioedema spectabilis were evaluated against cancer cell lines A-549 and HeLa.

Two new cytotoxic disulfated holostane glycosides from the sea cucumber Pentacta quadrangularis

Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and M