Catalpol

Base Information

• Chemical Name: Catalpol
• CAS No.: 2415-24-9
• Molecular Formula: C15H22O10
• Molecular Weight: 362.334
• Hs Code.: 29389090
• European Community (EC) Number: 219-324-0
• Wikipedia: Catalpol
• Mol file: 2415-24-9.mol

Synonyms:Catalpol(7CI,8CI);b-D-Glucopyranoside,1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl,[1aS-(1aa,1bb,2b,5ab,6b,6aa)]-;Catalpinoside;De(p-hydroxybenzoyl)catalposide;

Chemical Property of Catalpol

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 3.77E-21mmHg at 25°C
• Melting Point: 203-205 °C
• Refractive Index: 1.679
• Boiling Point: 675.6 °C at 760 mmHg
• PKA: 12.79±0.70(Predicted)
• Flash Point: 362.4 °C
• PSA: 161.60000
• Density: 1.72 g/cm³
• LogP: -3.59030
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 362.12129689
• Heavy Atom Count: 25
• Complexity: 542

Purity/Quality:

99% ^*data from raw suppliers

Catalpol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=COC(C2C1C(C3C2(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O
• Isomeric SMILES: C1=CO[C@@H]([C@@H]2[C@H]1[C@H]([C@@H]3[C@]2(O3)CO)O)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O
• Description: Catalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties. It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 μM. Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 μg/ml and 25 to 100 mg/kg, respectively. In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.
• Uses: Catapol is an iridoid glucoside that has been shown to alleviate neuropathic pain.

Technology Process of Catalpol

There total 18 articles about Catalpol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

6-O-[(E)-3,4-dimethoxycinnamoyl]catalpol (147714-71-4) → catalpol (2415-24-9)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; In tetrahydrofuran; ethanol; water; at 100 - 110 ℃; for 6h;

DOI:10.1039/d1ra00441g

Reference yield: 64.0%

4,4'-dimethoxy-β-truxinic acid catalpol diester → catalpol (2415-24-9) + dimethyl (1R*,2S*,3R*,4S*)-3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate (36650-62-1)

Guidance literature:

With sodium hydroxide; In methanol; at 18 ℃; for 5h;

DOI:10.1248/cpb.48.542

Reference yield: 36.0%

(E)-3-(4-Methoxy-phenyl)-acrylic acid (1S,4aR,5S,6R,7S,7aS)-6-chloro-5,7-dihydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-7-ylmethyl ester → catalpol (2415-24-9)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0031-9422(97)80017-9

upstream raw materials:

2',3',4',6,6',10-Hexaacetylcatalpol

6-O-(3,4-dihydroxybenzoyl)catalpol

rehmannioside B

2',3',4',6',10-Pentaacetyl-6-(4-acetylvanilloyl)catalpol

Downstream raw materials:

(1aS,1bS,2R,5aR,6S,6aS)-1a-Hydroxymethyl-1a,1b,2,5a,6,6a-hexahydro-1,3-dioxa-cyclopropa[a]indene-2,6-diol

2',3',4',6-Tetraacetyl-6',10-bis(triphenylmethyl)catalpol

Toluene-4-sulfonic acid (1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester

(1S,2S,6R,7R)-(-)-2-(Benzylthio)-7-hydroxy-3-oxabicyclo<4.3.0>nonan-9-on

Refernces

• 1、 Jensen, Soren R.,Gotfredsen, Charlotte H.,Harput, U. Sebnem,Saracoglu, Iclal. "Chlorinated iridoid glucosides from Veronica longifolia and their antioxidant activity". . p. 1593 - 1596. Retrieved 2010.
• 2、 Lunn et al.. "". . p. 104,109. Retrieved 1962.
• 3、 Afifi-Yazar,Sticher. "Verproside, a new iridoid glucoside from Veronica officinalis L. (Scrophulariaceae)". . p. 1905 - 1907. Retrieved 1980.
• 4、 Ali, Bakhat,Fatima, Itrat,Malik, Abdul,Ahmed, Zaheer. "New glycosidic constituents of abutilon Pakistanicum". experimental part. p. 2245 - 2250. Retrieved 2011/01/12.