SAXITOXIN

Base Information

• Chemical Name: SAXITOXIN
• CAS No.: 35523-89-8
• Molecular Formula: C10H17 N7 O4
• Molecular Weight: 301.305
• Mol file: 35523-89-8.mol

Synonyms:1H,10H-Pyrrolo[1,2-c]purine-10,10-diol,2,6-diamino-4-[[(aminocarbonyl)oxy]methyl]-3a,4,8,9-tetrahydro-, [3aS-(3aa,4a,10aR*)]-;Saxitoxin (7CI,8CI);(+)-Saxitoxin;STX;Saxitoxin hydrate;

Chemical Property of SAXITOXIN

Chemical Property:

• Refractive Index: 1.6400 (estimate)
• Boiling Point: 440.62°C (rough estimate)
• PKA: 13.32±0.50(Predicted)
• PSA: 184.81000
• Density: 1.3010 (rough estimate)
• LogP: -2.61320
• Storage Temp.: −20°C

Purity/Quality:

Safty Information:

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Description: First recognized in 1957 by Shantz et al. in the butter clam Saxidomus giganteus, saxitoxin is a naturally occurring toxin that is synthesized by various marine dinoflagellates and cyanobacteria. It is used in neurochemical and molecular biology research, but regulatory concerns have focused on its weaponization and potent toxicological effects on animals and humans. Saxitoxin causes paralytic shellfish poisoning (PSP) in humans and other animals; whales having ingested organisms contaminated with the toxin have died just hours after exposure. In humans, PSP can occur as a result of consuming shellfish or other seafood in which saxitoxin has accumulated. While effects have been documented worldwide, the sources of contaminated seafood have been identified as primarily the west and east coasts of the United States. To date, more than 30 different saxitoxin analogs have been identified. These include pure saxitoxin (STX), neosaxitoxin (neoSTX), the gonyautoxins (GTX), and decarbamoylsaxitoxin (dc-STX); of these, STX, 6NeoSTX, GTX1, and dc-STX seem to be the most toxic. The term saxitoxin typically refers to this collection of compounds produced naturally by cyanobacteria. Saxitoxin is far more potent than the classic puffer fish toxin tetrodotoxin, and is one of only two naturally occurring Schedule 1 chemical warfare agents (the other is ricin). In 1970, President Nixon ordered stocks of the toxin destroyed in compliance with U.N. agreements on biological weapons; however, the Central Intelligence Agency revealed in 1975 that there was a remaining supply, which was distributed to research facilities by the National Institutes of Health in order to study neurological diseases.
• Uses: As a Schedule 1 controlled substance under the Chemical Weapons Convention of 1993, the use of saxitoxin is extremely limited outside of weaponized forms. Its use as a chemical reagent in research is its other important use, as it has been instrumental in experiments to elucidate the mechanisms involved in sodium channels used in cellular communication. Mussel poison; clam poison; paralytic shellfish poison; gonyaulax toxin. These poisonous shellfish have been connected to instances of toxic”red-tides” where the high concentration of algae discoloring the water were of the Gonyaulax genus. Used as a too Saxitoxin is an alkaloid of nonplant origin.It is the neurotoxic constituent of dinoflagel lates (Gonyaulax catenella and G. excavata)the so-called “red tide” found along the U.S.coast. Shellfish, clams, and scallops consumethis and become extremely poisonous forhuman consumption.

Technology Process of SAXITOXIN

There total 16 articles about SAXITOXIN 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: 55.0%

isocyanate de chlorosulfonyle (1189-71-5) + decarbamoylsaxitoxin hydrate → saxitoxin hydrate (35523-89-8)

Guidance literature:

DOI:10.1271/bbb1961.47.191

Reference yield:

21-sulfosaxitoxin (64296-25-9) → saxitoxin hydrate (35523-89-8)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)87312-8

Reference yield:

decarbamoylsaxitoxin hydrate → saxitoxin hydrate (35523-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid / 0 °C / rapid queching with cold, aqueous NH₄OAc

2: 0.1N HCl / 0.08 h / 100 °C

With hydrogenchloride; In formic acid;

DOI:10.1016/S0040-4039(00)87312-8

upstream raw materials:

isocyanate de chlorosulfonyle

21-sulfosaxitoxin

11α-hydroxysaxitoxin

11β-hydroxysaxitoxin sulfate

Downstream raw materials:

carbamoyl-N-sulfo-11β-hydroxysaxitoxin sulfate

Refernces

• 1、 Shimizu, Yuzuru,Hsu, Chien P.. "Confirmation of the Structures of Gonyautoxins I - IV by Correlation with Saxitoxin". . p. 314 - 315. Retrieved 1981.
• 2、 Lukowski, April L.,Ellinwood, Duncan C.,Hinze, Meagan E.,Deluca, Ryan J.,Du Bois,Hall, Sherwood,Narayan, Alison R. H.. "C-H Hydroxylation in Paralytic Shellfish Toxin Biosynthesis". . p. 11863 - 11869. Retrieved 2018.