Linamarin | CAS#554-35-8

MedKoo Cat#: 328066 | Name: Linamarin

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Description:

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

Linamarin, also known as Phaseolunatin, is a glucoside of acetone cyanohydrin found in the leaves and roots of cassava, lima beans, and flax. Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide; hence food uses of plants that contain significant quantities of linamarin require extensive preparation and detoxification.

Chemical Structure

Linamarin

CAS#554-35-8

Theoretical Analysis

MedKoo Cat#: 328066

Name: Linamarin

CAS#: 554-35-8

Chemical Formula: C10H17NO6

Exact Mass: 247.1056

Molecular Weight: 247.25

Elemental Analysis: C, 48.58; H, 6.93; N, 5.67; O, 38.83

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 315.00	2 Weeks
25mg	USD 625.00	2 Weeks

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Synonym

Linamarin; Phaseolunatin.

IUPAC/Chemical Name

2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile

InChi Key

QLTCHMYAEJEXBT-ZEBDFXRSSA-N

InChi Code

InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1

SMILES Code

CC(C)(O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C#N

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Linamarin, a natural compound, possesses anticancer activity.

In vitro activity:

Cytotoxic effects of linamarin on MCF-7, HT-29 and HL60 cells were determined using the MTT assay. This study thus describes a method for the isolation and purification of linamarin from cassava, as well as its cytotoxicity potential. Reference: Bioprocess Biosyst Eng. 2007 Jul;30(4):261-9. https://pubmed.ncbi.nlm.nih.gov/17566787/

In vivo activity:

Linamarin microinjected into the dorsal hippocampus produced hyperactivity and loss of motor coordination which became more evident as treatment time increased. In the swim test, rats treated with linamarin displayed lateral rotation beginning on the fourth day of microinjection. Reference: Neurologia. 2016 Oct;31(8):516-22. https://pubmed.ncbi.nlm.nih.gov/25524044/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	121.34
	Ethanol	10.0	40.45
	PBS (pH 7.2)	2.0	8.09

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 247.25 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.

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

Formulation protocol:

1. Idibie CA, Davids H, Iyuke SE. Cytotoxicity of purified cassava linamarin to a selected cancer cell lines. Bioprocess Biosyst Eng. 2007 Jul;30(4):261-9. doi: 10.1007/s00449-007-0122-3. PMID: 17566787. 2. Rivadeneyra-Domínguez E, Rodríguez-Landa JF. Motor impairments induced by microinjection of linamarin in the dorsal hippocampus of Wistar rats. Neurologia. 2016 Oct;31(8):516-22. English, Spanish. doi: 10.1016/j.nrl.2014.10.018. Epub 2014 Dec 15. PMID: 25524044. 3. Rivadeneyra-Domínguez E, Vázquez-Luna A, Rodríguez-Landa JF, Díaz-Sobac R. Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption. Food Chem Toxicol. 2013 Sep;59:230-5. doi: 10.1016/j.fct.2013.06.004. Epub 2013 Jun 15. PMID: 23778051.

In vitro protocol:

In vivo protocol:

1. Rivadeneyra-Domínguez E, Rodríguez-Landa JF. Motor impairments induced by microinjection of linamarin in the dorsal hippocampus of Wistar rats. Neurologia. 2016 Oct;31(8):516-22. English, Spanish. doi: 10.1016/j.nrl.2014.10.018. Epub 2014 Dec 15. PMID: 25524044. 2. Rivadeneyra-Domínguez E, Vázquez-Luna A, Rodríguez-Landa JF, Díaz-Sobac R. Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption. Food Chem Toxicol. 2013 Sep;59:230-5. doi: 10.1016/j.fct.2013.06.004. Epub 2013 Jun 15. PMID: 23778051.

1: Rivadeneyra-Domínguez E, Rodríguez-Landa JF. Motor impairments induced by microinjection of linamarin in the dorsal hippocampus of Wistar rats. Neurologia. 2016 Oct;31(8):516-22. doi: 10.1016/j.nrl.2014.10.018. English, Spanish. PubMed PMID: 25524044. 2: Kato Y, Terada H. [Determination method of linamarin in cassava products and beans by ultra high performance liquid chromatography with tandem mass spectrometry]. Shokuhin Eiseigaku Zasshi. 2014;55(3):162-6. Japanese. PubMed PMID: 24990764. 3: Hussein AS, Abdullah N, Ahmadun FR. In vitro degradation of poly (D, L-lactide-co-glycolide) nanoparticles loaded with linamarin. IET Nanobiotechnol. 2013 Jun;7(2):33-41. PubMed PMID: 24046903. 4: Rivadeneyra-Domínguez E, Vázquez-Luna A, Rodríguez-Landa JF, Díaz-Sobac R. Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption. Food Chem Toxicol. 2013 Sep;59:230-5. doi: 10.1016/j.fct.2013.06.004. PubMed PMID: 23778051. 5: Salimon J, Abdullah BM, Salih N. Rubber (Hevea brasiliensis) seed oil toxicity effect and Linamarin compound analysis. Lipids Health Dis. 2012 Jun 13;11:74. doi: 10.1186/1476-511X-11-74. PubMed PMID: 22694753; PubMed Central PMCID: PMC3475106. 6: Girald W, Collin A, Izquierdo M. Toxicity and delivery methods for the linamarase/linamarin/glucose oxidase system, when used against human glioma tumors implanted in the brain of nude rats. Cancer Lett. 2011 Dec 26;313(1):99-107. doi: 10.1016/j.canlet.2011.08.029. PubMed PMID: 21955616. 7: Jørgensen K, Morant AV, Morant M, Jensen NB, Olsen CE, Kannangara R, Motawia MS, Møller BL, Bak S. Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme. Plant Physiol. 2011 Jan;155(1):282-92. doi: 10.1104/pp.110.164053. PubMed PMID: 21045121; PubMed Central PMCID: PMC3075754. 8: Rojas MG, Morales-Ramos JA. Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis. J Chem Ecol. 2010 Dec;36(12):1354-62. doi: 10.1007/s10886-010-9872-5. PubMed PMID: 20953678. 9: Vasconcellos SP, Cereda MP, Cagnon JR, Foglio MA, Rodrigues RA, Manfio GP, Oliveira VM. In vitro degradation of linamarin by microorganisms isolated from cassava wastewater treatment lagoons. Braz J Microbiol. 2009 Oct;40(4):879-83. doi: 10.1590/S1517-838220090004000019. PubMed PMID: 24031436; PubMed Central PMCID: PMC3768581. 10: Li J, Li H, Zhu L, Song W, Li R, Wang D, Dou K. The adenovirus-mediated linamarase/linamarin suicide system: a potential strategy for the treatment of hepatocellular carcinoma. Cancer Lett. 2010 Mar 28;289(2):217-27. doi: 10.1016/j.canlet.2009.08.016. PubMed PMID: 19733963. 11: Chen MH, Ma J, Li HM, Li J, Li R, Zhang FQ, Dou KF. [The killing effect and bystander effect of linamarase/linamarin suicide gene system on human hepatocellular carcinoma cell line HepG2 in vitro]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2008 Mar;24(3):274-7. Chinese. PubMed PMID: 18328192. 12: Idibie CA, Davids H, Iyuke SE. Cytotoxicity of purified cassava linamarin to a selected cancer cell lines. Bioprocess Biosyst Eng. 2007 Jul;30(4):261-9. PubMed PMID: 17566787. 13: Forslund K, Morant M, Jørgensen B, Olsen CE, Asamizu E, Sato S, Tabata S, Bak S. Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus. Plant Physiol. 2004 May;135(1):71-84. PubMed PMID: 15122013; PubMed Central PMCID: PMC429334. 14: Sreeja VG, Nagahara N, Li Q, Minami M. New aspects in pathogenesis of konzo: neural cell damage directly caused by linamarin contained in cassava (Manihot esculenta Crantz). Br J Nutr. 2003 Aug;90(2):467-72. PubMed PMID: 12908909. 15: Cortés ML, García-Escudero V, Hughes M, Izquierdo M. Cyanide bystander effect of the linamarase/linamarin killer-suicide gene therapy system. J Gene Med. 2002 Jul-Aug;4(4):407-14. PubMed PMID: 12124983. 16: Ruengprapavut S, Chulavatnatol M. New chemiluminescence assay for linamarin. IUBMB Life. 1999 Aug;48(2):219-23. PubMed PMID: 10794601. 17: Andersen MD, Busk PK, Svendsen I, Møller BL. Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes. J Biol Chem. 2000 Jan 21;275(3):1966-75. PubMed PMID: 10636899. 18: Nambisan B. Cassava latex as a source of linamarase for determination of linamarin. J Agric Food Chem. 1999 Feb;47(2):372-3. PubMed PMID: 10563902. 19: Carlsson L, Mlingi N, Juma A, Ronquist G, Rosling H. Metabolic fates in humans of linamarin in cassava flour ingested as stiff porridge. Food Chem Toxicol. 1999 Apr;37(4):307-12. PubMed PMID: 10418947. 20: Cliff J, Nicala D, Saute F, Givragy R, Azambuja G, Taela A, Chavane L, Gani A. Ankle clonus and thiocyanate, linamarin, and inorganic sulphate excretion in school children in communities with Konzo, Mozambique. J Trop Pediatr. 1999 Jun;45(3):139-42. PubMed PMID: 10401190.