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MedKoo Cat#: 597038 | Name: Domoic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Domoic acid is a kainic acid analog, heterocyclic amino acid from seaweed.

Chemical Structure

Domoic acid
Domoic acid
CAS#14277-97-5

Theoretical Analysis

MedKoo Cat#: 597038

Name: Domoic acid

CAS#: 14277-97-5

Chemical Formula: C15H21NO6

Exact Mass: 311.1369

Molecular Weight: 311.33

Elemental Analysis: C, 57.87; H, 6.80; N, 4.50; O, 30.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Domoic acid; L-Domoic acid; NSC 288031; NSC-288031; NSC288031;
IUPAC/Chemical Name
(2S,3S,4S)-4-((R,2Z,4E)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
InChi Key
VZFRNCSOCOPNDB-AOKDLOFSSA-N
InChi Code
InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1
SMILES Code
O=C(O)C[C@@H]1[C@@H](C(O)=O)NC[C@@H]1/C(C)=C\C=C\[C@H](C(O)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 311.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gai FF, Hedemand CK, Louw DC, Grobler K, Krock B, Moestrup Ø, Lundholm N. Morphological, molecular and toxigenic characteristics of Namibian Pseudo-nitzschia species - including Pseudo-nitzschia bucculenta sp. nov. Harmful Algae. 2018 Jun;76:80-95. doi: 10.1016/j.hal.2018.05.003. Epub 2018 May 31. PubMed PMID: 29887207. 2: Louw DC, Doucette GJ, Lundholm N. Morphology and toxicity of Pseudo-nitzschia species in the northern Benguela Upwelling System. Harmful Algae. 2018 May;75:118-128. doi: 10.1016/j.hal.2018.04.008. Epub 2018 May 3. PubMed PMID: 29778221. 3: Beach DG, Kerrin ES, Thomas K, Quilliam MA, McCarron P. Capillary electrophoresis-tandem mass spectrometry for multiclass analysis of polar marine toxins. Anal Bioanal Chem. 2018 May 16. doi: 10.1007/s00216-018-1089-4. [Epub ahead of print] PubMed PMID: 29767301. 4: Sanchis A, Salvador JP, Campbell K, Elliott CT, Shelver WL, Li QX, Marco MP. Fluorescent microarray for multiplexed quantification of environmental contaminants in seawater samples. Talanta. 2018 Jul 1;184:499-506. doi: 10.1016/j.talanta.2018.03.036. Epub 2018 Mar 16. PubMed PMID: 29674074. 5: Radad K, Al-Shraim M, Al-Emam A, Moldzio R, Rausch WD. Neurotoxic effects of domoic acid on dopaminergic neurons in primary mesencephalic cell culture. Folia Neuropathol. 2018;56(1):39-48. doi: 10.5114/fn.2018.74658. PubMed PMID: 29663739. 6: Ajani PA, Verma A, Lassudrie M, Doblin MA, Murray SA. A new diatom species P. hallegraeffii sp. nov. belonging to the toxic genus Pseudo-nitzschia (Bacillariophyceae) from the East Australian Current. PLoS One. 2018 Apr 12;13(4):e0195622. doi: 10.1371/journal.pone.0195622. eCollection 2018. PubMed PMID: 29649303; PubMed Central PMCID: PMC5896966. 7: Lee J, Sison-Mangus M. A Bayesian Semiparametric Regression Model for Joint Analysis of Microbiome Data. Front Microbiol. 2018 Mar 26;9:522. doi: 10.3389/fmicb.2018.00522. eCollection 2018. PubMed PMID: 29632519; PubMed Central PMCID: PMC5879107. 8: Demars F, Clark K, Wyeth MS, Abrams E, Buckmaster PS. A single subconvulsant dose of domoic acid at mid-gestation does not cause temporal lobe epilepsy in mice. Neurotoxicology. 2018 May;66:128-137. doi: 10.1016/j.neuro.2018.04.001. Epub 2018 Apr 3. PubMed PMID: 29625197; PubMed Central PMCID: PMC5940543. 9: Peacock MB, Gibble CM, Senn DB, Cloern JE, Kudela RM. Blurred lines: Multiple freshwater and marine algal toxins at the land-sea interface of San Francisco Bay, California. Harmful Algae. 2018 Mar;73:138-147. doi: 10.1016/j.hal.2018.02.005. Epub 2018 Mar 10. PubMed PMID: 29602502. 10: Radan RL, Cochlan WP. Differential toxin response of Pseudo-nitzschia multiseries as a function of nitrogen speciation in batch and continuous cultures, and during a natural assemblage experiment. Harmful Algae. 2018 Mar;73:12-29. doi: 10.1016/j.hal.2018.01.002. Epub 2018 Feb 4. PubMed PMID: 29602500. 11: Gibble C, Duerr R, Bodenstein B, Lindquist K, Lindsey J, Beck J, Henkel L, Roletto J, Harvey J, Kudela R. Investigation of a Largescale Common Murre ( Uria aalge) Mortality Event in California in 2015. J Wildl Dis. 2018 Mar 16. doi: 10.7589/2017-07-179. [Epub ahead of print] PubMed PMID: 29547358. 12: Grattan LM, Boushey CJ, Liang Y, Lefebvre KA, Castellon LJ, Roberts KA, Toben AC, Morris JG. Repeated Dietary Exposure to Low Levels of Domoic Acid and Problems with Everyday Memory: Research to Public Health Outreach. Toxins (Basel). 2018 Feb 28;10(3). pii: E103. doi: 10.3390/toxins10030103. PubMed PMID: 29495583; PubMed Central PMCID: PMC5869391. 13: Ao J, Gu J, Yuan T, Li D, Ma Y, Shen Z. Applying molecular modelling and experimental studies to develop molecularly imprinted polymer for domoic acid enrichment from both seawater and shellfish. Chemosphere. 2018 May;199:98-106. doi: 10.1016/j.chemosphere.2018.02.005. Epub 2018 Feb 3. PubMed PMID: 29433033. 14: Dursun F, Ünlü S, Yurdun T. Determination of Domoic Acid in Plankton Net Samples from Golden Horn Estuary, Turkey, Using HPLC with Fluorescence Detection. Bull Environ Contam Toxicol. 2018 Mar;100(3):457-462. doi: 10.1007/s00128-018-2275-y. Epub 2018 Jan 24. PubMed PMID: 29368303. 15: Maeno Y, Kotaki Y, Terada R, Cho Y, Konoki K, Yotsu-Yamashita M. Six domoic acid related compounds from the red alga, Chondria armata, and domoic acid biosynthesis by the diatom, Pseudo-nitzschia multiseries. Sci Rep. 2018 Jan 10;8(1):356. doi: 10.1038/s41598-017-18651-w. PubMed PMID: 29321590; PubMed Central PMCID: PMC5762911. 16: Yang F, Wang R, Na G, Yan Q, Lin Z, Zhang Z. Preparation and application of a molecularly imprinted monolith for specific recognition of domoic acid. Anal Bioanal Chem. 2018 Feb;410(6):1845-1854. doi: 10.1007/s00216-017-0843-3. Epub 2018 Jan 9. PubMed PMID: 29313078. 17: Yamamoto A, Kudo S, Nakaya M, Hanaishi R, Masuda Y, Kimura J, Sakuraba A, Shibata M, Kudo S, Itsukaichi T, Sato H, Murakami A, Kogawa A. [Validation Study of Analytical Method for Determination of Amnesic Shellfish Poison in Bivalves]. Shokuhin Eiseigaku Zasshi. 2017;58(6):281-287. doi: 10.3358/shokueishi.58.281. Japanese. PubMed PMID: 29311448. 18: Smith ME, Swoboda HD. Toxicity, Shellfish. 2017 Nov 20. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK470225/ PubMed PMID: 29262048. 19: Lopes VM, Rosa R, Costa PR. Presence and persistence of the amnesic shellfish poisoning toxin, domoic acid, in octopus and cuttlefish brains. Mar Environ Res. 2018 Feb;133:45-48. doi: 10.1016/j.marenvres.2017.12.001. Epub 2017 Dec 5. PubMed PMID: 29223596. 20: Bowers HA, Marin R 3rd, Birch JM, Scholin CA. Sandwich hybridization probes for the detection of Pseudo-nitzschia (Bacillariophyceae) species: An update to existing probes and a description of new probes. Harmful Algae. 2017 Dec;70:37-51. doi: 10.1016/j.hal.2017.10.005. Epub 2017 Nov 1. PubMed PMID: 29169567.