Monocrotalic acid

Base Information

• Chemical Name: Monocrotalic acid
• CAS No.: 26543-09-9
• Molecular Formula: C8H12 O5
• Molecular Weight: 188.20
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID501169173
• Nikkaji Number: J49.586G
• Mol file: 26543-09-9.mol

Synonyms:Monocrotalic acid;26543-09-9;(2R,3R,4R)-3-Hydroxy-2,3,4-trimethyl-5-oxooxolane-2-carboxylic acid;L-Arabinaric acid, 2-deoxy-2-methyl-3,4-di-C-methyl-, 1,4-lactone;DTXSID501169173;AKOS040753124;(2R,3R,4R)-3-hydroxy-2,3,4-trimethyl-5-oxotetrahydrofuran-2-carboxylic acid

Chemical Property of Monocrotalic acid

Chemical Property:

• Vapor Pressure: 4E-08mmHg at 25°C
• Melting Point: 181-182 °C
• Boiling Point: 401.7°Cat760mmHg
• PKA: 2.69±0.60(Predicted)
• Flash Point: 166.7°C
• PSA: 83.83000
• Density: 1.322g/cm³
• LogP: -0.22640
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

MONOCROTALIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic.
• Hazard Codes: Moderately toxic.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)OC(C1(C)O)(C)C(=O)O
• Isomeric SMILES: C[C@H]1C(=O)O[C@@]([C@]1(C)O)(C)C(=O)O

Technology Process of Monocrotalic acid

There total 11 articles about Monocrotalic acid 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: 80.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → Monocrotalic acid (26543-09-9) + monocrotaline pyrrole (23291-96-5) + 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-(7-methoxy-6,7-dihydro-5H-pyrrolizin-1-ylmethyl)-5-methyl-1H-pyrimidine-2,4-dione (133787-49-2) + 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-(7-hydroxymethyl-2,3-dihydro-1H-pyrrolizin-1-ylmethyl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 25 ℃; for 5h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92122-1

Reference yield: 80.0%

2'-Deoxyguanosine (961-07-9) + monocrotaline pyrrole (23291-96-5) → Monocrotalic acid (26543-09-9) + dehydroretronecine dimethyl ether (28333-17-7) + 9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-[(7-methoxy-2,3-dihydro-1H-pyrrolizin-1-ylmethyl)-amino]-1,9-dihydro-purin-6-one + C19H24N6O5 (133787-47-0)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 25 ℃; for 5h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92122-1

Reference yield: 80.0%

monocrotaline pyrrole (23291-96-5) + 2'-Deoxycytidine (951-77-9) → Monocrotalic acid (26543-09-9) + dehydroretronecine dimethyl ether (28333-17-7) + 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-3-(7-methoxy-6,7-dihydro-5H-pyrrolizin-1-ylmethyl)-3,4-dihydro-1H-pyrimidin-2-one (133787-51-6,133787-55-0)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 25 ℃; for 5h;

DOI:10.1016/S0040-4039(00)92122-1

upstream raw materials:

monocrotaline

2'-Deoxyguanosine

monocrotaline pyrrole

cropodine

Refernces

• 1、 Adams,Hauserman. "-". . p. 694,698. Retrieved 1952.
• 2、 Niwa,Ogawa,Okamoto,Yamada. "Alkylation of nucleosides by dehydromonocrotaline, the putative toxic metabolite of the carcinogenic pyrrolizidine alkaloid monocrotaline". . p. 927 - 930. Retrieved 2007/10/02.