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MedKoo Cat#: 592604 | Name: Mandelonitrile glucoside

Description:

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

Mandelonitrile glucoside is a Cyanogenic glycoside.

Chemical Structure

Mandelonitrile glucoside
Mandelonitrile glucoside
CAS#138-53-4

Theoretical Analysis

MedKoo Cat#: 592604

Name: Mandelonitrile glucoside

CAS#: 138-53-4

Chemical Formula: C14H17NO6

Exact Mass: 295.1056

Molecular Weight: 295.29

Elemental Analysis: C, 56.95; H, 5.80; N, 4.74; O, 32.51

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
Prulaurasin; Mandelonitrile glucoside
IUPAC/Chemical Name
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)- (9CI)
InChi Key
ZKSZEJFBGODIJW-MXNNCRBYSA-N
InChi Code
InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9?,10-,11-,12+,13-,14-/m1/s1
SMILES Code
N#CC(O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C2=CC=CC=C2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 295.29 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: Mizushina Y, Takahashi N, Ogawa A, Tsurugaya K, Koshino H, Takemura M, Yoshida S, Matsukage A, Sugawara F, Sakaguchi K. The cyanogenic glucoside, prunasin (D-mandelonitrile-beta-D-glucoside), is a novel inhibitor of DNA polymerase beta. J Biochem. 1999 Aug;126(2):430-6. PubMed PMID: 10423540. 2: Sakata M, Yoshida A, Yuasa C, Sakata K, Haga M. Toxicity of D, L-mandelonitrile-beta-D-glucoside, "prulaurasin" in rat. J Toxicol Sci. 1987 Feb;12(1):47-55. PubMed PMID: 3599103. 3: Lee HM, Moon A. Amygdalin Regulates Apoptosis and Adhesion in Hs578T Triple-Negative Breast Cancer Cells. Biomol Ther (Seoul). 2016 Jan;24(1):62-6. doi: 10.4062/biomolther.2015.172. Epub 2016 Jan 1. PubMed PMID: 26759703; PubMed Central PMCID: PMC4703354. 4: Vesely DL, Benson WR, Sheinin EB, Levey GS. Two components of laetrile (mandelonitrile and cyanide) stimulate guanylate cyclase activity. Proc Soc Exp Biol Med. 1979 Jul;161(3):319-21. PubMed PMID: 37525. 5: Fenselau C, Pallante S, Batzinger RP, Benson WR, Barron RP, Sheinin EB, Maienthal M. Mandelonitrile beta-glucuronide: synthesis and characterization. Science. 1977 Nov 11;198(4317):625-7. PubMed PMID: 335509. 6: Menon R, Munjal N, Sturino JM. Characterization of amygdalin-degrading Lactobacillus species. J Appl Microbiol. 2015 Feb;118(2):443-53. doi: 10.1111/jam.12704. Epub 2015 Jan 9. PubMed PMID: 25421573. 7: Miller RE, Tuck KL. Reports on the distribution of aromatic cyanogenic glycosides in Australian tropical rainforest tree species of the Lauraceae and Sapindaceae. Phytochemistry. 2013 Aug;92:146-52. doi: 10.1016/j.phytochem.2013.04.007. Epub 2013 May 2. PubMed PMID: 23642385. 8: Hösel W, Tober I, Eklund SH, Conn EE. Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings. Arch Biochem Biophys. 1987 Jan;252(1):152-62. PubMed PMID: 3101594. 9: Rauws AG, Olling M, Timmerman A. The pharmacokinetics of amygdalin. Arch Toxicol. 1982 Mar;49(3-4):311-9. PubMed PMID: 7092570. 10: Wu HC, Poulton JE. Immunocytochemical Localization of Mandelonitrile Lyase in Mature Black Cherry (Prunus serotina Ehrh.) Seeds. Plant Physiol. 1991 Aug;96(4):1329-37. PubMed PMID: 16668338; PubMed Central PMCID: PMC1080934. 11: Chang HK, Shin MS, Yang HY, Lee JW, Kim YS, Lee MH, Kim J, Kim KH, Kim CJ. Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells. Biol Pharm Bull. 2006 Aug;29(8):1597-602. PubMed PMID: 16880611. 12: Gopalan V, Pastuszyn A, Galey WR Jr, Glew RH. Exolytic hydrolysis of toxic plant glucosides by guinea pig liver cytosolic beta-glucosidase. J Biol Chem. 1992 Jul 15;267(20):14027-32. PubMed PMID: 1629201. 13: De Nicola GR, Leoni O, Malaguti L, Bernardi R, Lazzeri L. A simple analytical method for dhurrin content evaluation in cyanogenic plants for their utilization in fodder and biofumigation. J Agric Food Chem. 2011 Aug 10;59(15):8065-9. doi: 10.1021/jf200754f. Epub 2011 Jul 11. PubMed PMID: 21707058. 14: Berenguer-Navarro V, Giner-Galván RM, Grané-Teruel N, Arrazola-Paternina G. Chromatographic determination of cyanoglycosides prunasin and amygdalin in plant extracts using a porous graphitic carbon column. J Agric Food Chem. 2002 Nov 20;50(24):6960-3. PubMed PMID: 12428943. 15: Shim SM, Kwon H. Metabolites of amygdalin under simulated human digestive fluids. Int J Food Sci Nutr. 2010 Dec;61(8):770-9. doi: 10.3109/09637481003796314. Epub 2010 Jun 9. PubMed PMID: 20528582. 16: Jones PR, Moller BL, Hoj PB. The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity. J Biol Chem. 1999 Dec 10;274(50):35483-91. PubMed PMID: 10585420. 17: Czjzek M, Cicek M, Zamboni V, Bevan DR, Henrissat B, Esen A. The mechanism of substrate (aglycone) specificity in beta -glucosidases is revealed by crystal structures of mutant maize beta -glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes. Proc Natl Acad Sci U S A. 2000 Dec 5;97(25):13555-60. PubMed PMID: 11106394; PubMed Central PMCID: PMC17614. 18: Silva MC, Terra WR, Ferreira C. The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae. Insect Biochem Mol Biol. 2004 Oct;34(10):1089-99. PubMed PMID: 15475303. 19: Verdoucq L, Morinière J, Bevan DR, Esen A, Vasella A, Henrissat B, Czjze M. Structural determinants of substrate specificity in family 1 beta-glucosidases: novel insights from the crystal structure of sorghum dhurrinase-1, a plant beta-glucosidase with strict specificity, in complex with its natural substrate. J Biol Chem. 2004 Jul 23;279(30):31796-803. Epub 2004 May 17. PubMed PMID: 15148317. 20: Nahrstedt A. Cyanogenesis and the role of cyanogenic compounds in insects. Ciba Found Symp. 1988;140:131-50. Review. PubMed PMID: 3073053.