Lotaustralin | CAS#534-67-8 | cyanogenic glycoside

MedKoo Cat#: 599255 | Name: Lotaustralin

Featured

Description:

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

Lotaustralin is a cyanogenic glycoside.

Chemical Structure

Lotaustralin

CAS#534-67-8

Theoretical Analysis

MedKoo Cat#: 599255

Name: Lotaustralin

CAS#: 534-67-8

Chemical Formula: C11H19NO6

Exact Mass: 261.1212

Molecular Weight: 261.27

Elemental Analysis: C, 50.57; H, 7.33; N, 5.36; O, 36.74

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 565.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Lotaustralin;

IUPAC/Chemical Name

(R)-2-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanenitrile

InChi Key

WEWBWVMTOYUPHH-QHAQEBJBSA-N

InChi Code

InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1

SMILES Code

CC[C@@](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

>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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lotaustralin is a cyanogenic glycoside.

In vitro activity:

TBD

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 261.27 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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: 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. 2: 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. Epub 2010 Nov 2. PubMed PMID: 21045121; PubMed Central PMCID: PMC3075754. 3: Akgul Y, Ferreira D, Abourashed EA, Khan IA. Lotaustralin from Rhodiola rosea roots. Fitoterapia. 2004 Sep;75(6):612-4. PubMed PMID: 15351122. 4: Kang S, Wang J, Zhang J, Liu F, Xu Z. [Quantitative analysis of salidroside and lotaustralin in Rhodiola by gas chromatography]. Zhongguo Zhong Yao Za Zhi. 1998 Jun;23(6):365-6, 384. Chinese. PubMed PMID: 11601302. 5: BUTLER GW, CONN EE. BIOSYNTHESIS OF THE CYANOGENIC GLUCOSIDES LINAMARIN AND LOTAUSTRALIN. I. LABELING STUDIES IN VIVO WITH LINUM USITATISSIMUM. J Biol Chem. 1964 Jun;239:1674-9. PubMed PMID: 14213333. 6: 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. Epub 2010 Oct 16. PubMed PMID: 20953678. 7: Fürstenberg-Hägg J, Zagrobelny M, Jørgensen K, Vogel H, Møller BL, Bak S. Chemical defense balanced by sequestration and de novo biosynthesis in a lepidopteran specialist. PLoS One. 2014 Oct 9;9(10):e108745. doi: 10.1371/journal.pone.0108745. eCollection 2014. PubMed PMID: 25299618; PubMed Central PMCID: PMC4191964. 8: 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. 9: Muzashvili T, Moniuszko-Szajwaj B, Pecio L, Oleszek W, Stochmal A. Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in Trifolium species. J Agric Food Chem. 2014 Feb 26;62(8):1777-82. doi: 10.1021/jf4056659. Epub 2014 Feb 12. PubMed PMID: 24476020. 10: Nahrstedt A, Davis RH. Cyanogenic glycosides in butterflies: detection and synthesis of linamarin and lotaustralin in the heliconiinae. Planta Med. 1981 Jun;42(6):124-5. PubMed PMID: 17401921. 11: TETLEY JH. Inhibition of populations of Haemonchus contortus in sheep fed on white clover (Trifolium repens) high in lotaustralin. Nature. 1953 Feb 14;171(4346):311. PubMed PMID: 13036873. 12: Dalisay DS, Kim KW, Lee C, Yang H, Rübel O, Bowen BP, Davin LB, Lewis NG. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging. J Nat Prod. 2015 Jun 26;78(6):1231-42. doi: 10.1021/acs.jnatprod.5b00023. Epub 2015 May 17. PubMed PMID: 25981198. 13: Zilg H, Conn EE. Stereochemical aspects of lotaustralin biosynthesis. J Biol Chem. 1974 May 25;249(10):3112-5. PubMed PMID: 4406603. 14: Lai D, Abou Hachem M, Robson F, Olsen CE, Wang TL, Møller BL, Takos AM, Rook F. The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous β-glucosidases resulting from a crucial amino acid substitution. Plant J. 2014 Jul;79(2):299-311. doi: 10.1111/tpj.12561. Epub 2014 Jun 23. PubMed PMID: 24861854. 15: Zilg H, Tapper BA, Conn EE. The origin of the glucosidic linkage oxygen of the cyanogenic glucosides, linamarin and lotaustralin. J Biol Chem. 1972 Apr 25;247(8):2384-6. PubMed PMID: 5019952. 16: Sulyok M, Beed F, Boni S, Abass A, Mukunzi A, Krska R. Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(4):488-502. doi: 10.1080/19440049.2014.975752. Epub 2014 Nov 14. PubMed PMID: 25350522. 17: Lai D, Pičmanová M, Abou Hachem M, Motawia MS, Olsen CE, Møller BL, Rook F, Takos AM. Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs. Plant Mol Biol. 2015 Sep;89(1-2):21-34. doi: 10.1007/s11103-015-0348-4. Epub 2015 Aug 7. PubMed PMID: 26249044. 18: Siegień I, Adamczuk A, Wróblewska K. Light affects in vitro organogenesis of Linum usitatissimum L. and its cyanogenic potential. Acta Physiol Plant. 2013;35(3):781-789. Epub 2012 Oct 12. PubMed PMID: 25834293; PubMed Central PMCID: PMC4372823. 19: Song L, Shi JG, Lin S, Yang YC, Yao CS. [Chemical constituents from the linseed meal]. Yao Xue Xue Bao. 2013 Apr;48(4):521-5. Chinese. PubMed PMID: 23833939. 20: Kannangara R, Motawia MS, Hansen NK, Paquette SM, Olsen CE, Møller BL, Jørgensen K. Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava. Plant J. 2011 Oct;68(2):287-301. doi: 10.1111/j.1365-313X.2011.04695.x. Epub 2011 Aug 19. PubMed PMID: 21736650.