Molecular structure of Lotaustralin, CAS Number: 534-67-8
Lotaustralin (CAS 534-67-8)
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Alternate Names:
(R)-2-(β-D-Glucopyranosyloxy)-2-methylbutyronitrile; (2R)-2-(β-D-Glucopyranosyloxy)-2-methyl-butanenitrile
Application:
Lotaustralin is a carbohydrate derivative
CAS Number:
534-67-8
Molecular Weight:
261.27
Molecular Formula:
C11H19NO6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Lotaustralin is a cyanogenic glucoside found in trace amounts in a wide variety of plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, an acetone cyanohydrin glucoside also found in plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.
Lotaustralin (CAS 534-67-8) References
- [Quantitative analysis of salidroside and lotaustralin in Rhodiola by gas chromatography]. | Kang, S., et al. 1998. Zhongguo Zhong Yao Za Zhi. 23: 365-6, 384. PMID: 11601302
- Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus. | Forslund, K., et al. 2004. Plant Physiol. 135: 71-84. PMID: 15122013
- Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus). | Frehner, M., et al. 1990. Plant Physiol. 94: 28-34. PMID: 16667698
- The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles. | Zagrobelny, M., et al. 2007. Insect Biochem Mol Biol. 37: 10-8. PMID: 17175442
- Cyanogenic glycosides in butterflies: detection and synthesis of linamarin and lotaustralin in the heliconiinae. | Nahrstedt, A. and Davis, RH. 1981. Planta Med. 42: 124-5. PMID: 17401921
- Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis. | Rojas, MG. and Morales-Ramos, JA. 2010. J Chem Ecol. 36: 1354-62. PMID: 20953678
- Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme. | Jørgensen, K., et al. 2011. Plant Physiol. 155: 282-92. PMID: 21045121
- Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in Trifolium species. | Muzashvili, T., et al. 2014. J Agric Food Chem. 62: 1777-82. PMID: 24476020
- 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. | Lai, D., et al. 2014. Plant J. 79: 299-311. PMID: 24861854
- Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defenses. | Lai, D., et al. 2020. Plant Direct. 4: e00244. PMID: 32775954
- Properties of a microsomal enzyme system from Linum usitatissimum (linen flax) which oxidizes valine to acetone cyanohydrin and isoleucine to 2-methylbutanone cyanohydrin. | Cutler, AJ., et al. 1985. Arch Biochem Biophys. 238: 272-9. PMID: 3985623
- Cyanogenic and non-cyanogenic glycosides from Manihot esculenta. | Prawat, H., et al. 1995. Phytochemistry. 40: 1167-73. PMID: 7492370
- Bioactive constituents of Chinese natural medicines. IV. Rhodiolae radix. (2).: On the histamine release inhibitors from the underground part of Rhodiola sacra (Prain ex Hamet) S. H. Fu (Crassulaceae): chemical structures of rhodiocyanoside D and sacranosides A and B. | Yoshikawa, M., et al. 1997. Chem Pharm Bull (Tokyo). 45: 1498-503. PMID: 9332002
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Lotaustralin, 2.5 mg | sc-207835 | 2.5 mg | $622.00 | |||
Lotaustralin, 25 mg | sc-207835A | 25 mg | $3723.00 |