MedKoo Cat#: 598613 | Name: Lesquerolic acid

Description:

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

Lesquerolic acid is a hydroxy acid found in the oil of most species of Lesquerella

Chemical Structure

Lesquerolic acid
Lesquerolic acid
CAS#4103-20-2 (free)

Theoretical Analysis

MedKoo Cat#: 598613

Name: Lesquerolic acid

CAS#: 4103-20-2 (free)

Chemical Formula: C20H38O3

Exact Mass: 326.2821

Molecular Weight: 326.52

Elemental Analysis: C, 73.57; H, 11.73; O, 14.70

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 #
180641-01-4 (glycerol diester) 180641-02-5 (glycerol monoester) 4103-20-2 (free)
Synonym
Lesquerolic acid;
IUPAC/Chemical Name
(R,Z)-14-hydroxyicos-11-enoic acid
InChi Key
OONXYOAWMIVMCI-KWRJMZDGSA-N
InChi Code
InChI=1S/C20H38O3/c1-2-3-4-13-16-19(21)17-14-11-9-7-5-6-8-10-12-15-18-20(22)23/h11,14,19,21H,2-10,12-13,15-18H2,1H3,(H,22,23)/b14-11-/t19-/m1/s1
SMILES Code
CCCCCC[C@@H](O)C/C=C\CCCCCCCCCC(O)=O
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
>3 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 326.52 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: Cocuron JC, Anderson B, Boyd A, Alonso AP. Targeted metabolomics of Physaria fendleri, an industrial crop producing hydroxy fatty acids. Plant Cell Physiol. 2014 Mar;55(3):620-33. doi: 10.1093/pcp/pcu011. Epub 2014 Jan 18. PubMed PMID: 24443498. 2: Snapp AR, Kang J, Qi X, Lu C. A fatty acid condensing enzyme from Physaria fendleri increases hydroxy fatty acid accumulation in transgenic oilseeds of Camelina sativa. Planta. 2014 Sep;240(3):599-610. doi: 10.1007/s00425-014-2122-2. Epub 2014 Jul 15. PubMed PMID: 25023632. 3: Kuo TM, Rooney AP, Isbell TA. Conversion of lesquerolic acid to 14-oxo-11(Z)-eicosenoic acid by genetically variable Sphingobacterium multivorum strains. Curr Microbiol. 2008 Jul;57(1):55-60. doi: 10.1007/s00284-008-9152-6. Epub 2008 Apr 1. PubMed PMID: 18379841. 4: Chen GQ, van Erp H, Martin-Moreno J, Johnson K, Morales E, Browse J, Eastmond PJ, Lin JT. Expression of Castor LPAT2 Enhances Ricinoleic Acid Content at the sn-2 Position of Triacylglycerols in Lesquerella Seed. Int J Mol Sci. 2016 Apr 6;17(4):507. doi: 10.3390/ijms17040507. PubMed PMID: 27058535; PubMed Central PMCID: PMC4848963. 5: Smith MA, Moon H, Chowrira G, Kunst L. Heterologous expression of a fatty acid hydroxylase gene in developing seeds of Arabidopsis thaliana. Planta. 2003 Jul;217(3):507-16. Epub 2003 Mar 18. PubMed PMID: 14520576. 6: Moon H, Smith MA, Kunst L. A condensing enzyme from the seeds of Lesquerella fendleri that specifically elongates hydroxy fatty acids. Plant Physiol. 2001 Dec;127(4):1635-43. PubMed PMID: 11743108; PubMed Central PMCID: PMC133568. 7: Broun P, Somerville C. Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean. Plant Physiol. 1997 Mar;113(3):933-42. PubMed PMID: 9085577; PubMed Central PMCID: PMC158213. 8: Salywon AM, Dierig DA, Rebman JP, de Rodríguez DJ. Evaluation of new Lesquerella and Physaria (Brassicaceae) oilseed germplasm. Am J Bot. 2005 Jan;92(1):53-62. doi: 10.3732/ajb.92.1.53. PubMed PMID: 21652384. 9: Broun P, Shanklin J, Whittle E, Somerville C. Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science. 1998 Nov 13;282(5392):1315-7. PubMed PMID: 9812895. 10: Reed DW, Taylor DC, Covello PS. Metabolism of Hydroxy Fatty Acids in Developing Seeds in the Genera Lesquerella (Brassicaceae) and Linum (Linaceae). Plant Physiol. 1997 May;114(1):63-68. PubMed PMID: 12223689; PubMed Central PMCID: PMC158279.