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MedKoo Cat#: 598230 | Name: Laetrile

Description:

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

Laetrile is a cyanogenic glycoside found in the seeds of Rosaceae.

Chemical Structure

Laetrile
Laetrile
CAS#1332-94-1

Theoretical Analysis

MedKoo Cat#: 598230

Name: Laetrile

CAS#: 1332-94-1

Chemical Formula: C14H15NO7

Exact Mass: 309.0849

Molecular Weight: 309.27

Elemental Analysis: C, 54.37; H, 4.89; N, 4.53; O, 36.21

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 #
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Synonym
Laetrile; NSC 103055; NSC-103055; NSC103055; Mandelonitrile beta-glucuronide;
IUPAC/Chemical Name
(2S,3S,4S,5R,6R)-6-((R)-cyano(phenyl)methoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
InChi Key
XLSLFPQAPYONPW-WHUHBCJBSA-N
InChi Code
InChI=1S/C14H15NO7/c15-6-8(7-4-2-1-3-5-7)21-14-11(18)9(16)10(17)12(22-14)13(19)20/h1-5,8-12,14,16-18H,(H,19,20)/t8-,9-,10-,11+,12-,14+/m0/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](C(O)=O)O1)O)O)[C@@H]1O[C@@H](C#N)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 309.27 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.

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: Milazzo S, Ernst E, Lejeune S, Boehm K, Horneber M. Laetrile treatment for cancer. Cochrane Database Syst Rev. 2011 Nov 9;(11):CD005476. doi: 10.1002/14651858.CD005476.pub3. Review. Update in: Cochrane Database Syst Rev. 2015;4:CD005476. PubMed PMID: 22071824. 2: Zdrojewicz Z, Otlewska A, Hackemer P, Otlewska A. [Amygdalin - structure and clinical significance]. Pol Merkur Lekarski. 2015 May;38(227):300-3. Review. Polish. PubMed PMID: 26039028. 3: Moertel CG, Fleming TR, Rubin J, Kvols LK, Sarna G, Koch R, Currie VE, Young CW, Jones SE, Davignon JP. A clinical trial of amygdalin (Laetrile) in the treatment of human cancer. N Engl J Med. 1982 Jan 28;306(4):201-6. PubMed PMID: 7033783. 4: Song Z, Xu X. Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7. doi: 10.4103/0973-1482.139743. Review. PubMed PMID: 25207888. 5: Milazzo S, Lejeune S, Ernst E. Laetrile for cancer: a systematic review of the clinical evidence. Support Care Cancer. 2007 Jun;15(6):583-595. doi: 10.1007/s00520-006-0168-9. Epub 2006 Nov 15. Review. PubMed PMID: 17106659. 6: Bode AM, Dong Z. Toxic phytochemicals and their potential risks for human cancer. Cancer Prev Res (Phila). 2015 Jan;8(1):1-8. doi: 10.1158/1940-6207.CAPR-14-0160. Epub 2014 Oct 27. Review. PubMed PMID: 25348854; PubMed Central PMCID: PMC4289646. 7: Newell GR, Ellison NM. Ethics and designs: laetrile trials as an example. Cancer Treat Rep. 1980 Feb-Mar;64(2-3):363-5. PubMed PMID: 6996807. 8: Unproven methods of cancer management. Laetrile. CA Cancer J Clin. 1991 May-Jun;41(3):187-92. Review. PubMed PMID: 1902140. 9: Ellison NM, Byar DP, Newell GR. Special report on Laetrile: the NCI Laetrile Review. Results of the National Cancer Institute's retrospective Laetrile analysis. N Engl J Med. 1978 Sep 7;299(10):549-52. PubMed PMID: 683212. 10: Wahab MF, Breitbach ZS, Armstrong DW, Strattan R, Berthod A. Problems and Pitfalls in the Analysis of Amygdalin and Its Epimer. J Agric Food Chem. 2015 Oct 14;63(40):8966-73. doi: 10.1021/acs.jafc.5b03120. Epub 2015 Oct 2. PubMed PMID: 26431391. 11: Kapoor S. Safety of studies analysing clinical benefit of amygdalin. Immunopharmacol Immunotoxicol. 2014 Feb;36(1):87. doi: 10.3109/08923973.2013.861846. Epub 2014 Jan 8. Review. PubMed PMID: 24397550. 12: Willhite CC. Congenital malformations induced by laetrile. Science. 1982 Mar 19;215(4539):1513-5. PubMed PMID: 7063858. 13: Milazzo S, Ernst E, Lejeune S, Schmidt K. Laetrile treatment for cancer. Cochrane Database Syst Rev. 2006 Apr 19;(2):CD005476. Review. Update in: Cochrane Database Syst Rev. 2011;(11):CD005476. PubMed PMID: 16625640. 14: Jones GT, Abramson N. Laetrile: what we know and what we do about it. J Fla Med Assoc. 1979 May;66(5):548-52. PubMed PMID: 379271. 15: Li X, Shi F, Gu P, Liu L, He H, Ding L. A sensitive LC-MS/MS method for simultaneous determination of amygdalin and paeoniflorin in human plasma and its application. J Pharm Biomed Anal. 2014 Apr;92:160-4. doi: 10.1016/j.jpba.2014.01.020. Epub 2014 Jan 24. PubMed PMID: 24525563. 16: Blaheta RA, Nelson K, Haferkamp A, Juengel E. Amygdalin, quackery or cure? Phytomedicine. 2016 Apr 15;23(4):367-76. doi: 10.1016/j.phymed.2016.02.004. Epub 2016 Feb 17. Review. PubMed PMID: 27002407. 17: Bolarinwa IF, Orfila C, Morgan MR. Determination of amygdalin in apple seeds, fresh apples and processed apple juices. Food Chem. 2015 Mar 1;170:437-42. doi: 10.1016/j.foodchem.2014.08.083. Epub 2014 Aug 29. PubMed PMID: 25306368. 18: Price JH, Price JA. Laetrile--an overview. J Sch Health. 1978 Sep;48(7):409-16. PubMed PMID: 250579. 19: Santos Pimenta LP, Schilthuizen M, Verpoorte R, Choi YH. Quantitative analysis of amygdalin and prunasin in Prunus serotina Ehrh. using (1) H-NMR spectroscopy. Phytochem Anal. 2014 Mar-Apr;25(2):122-6. doi: 10.1002/pca.2476. Epub 2013 Sep 23. PubMed PMID: 24115144. 20: Yang QY, Song L, Zhang JF, Shen ZF, Liu Q, Liu SN, Zheng WS, Yao CS. Cyanogenetic glycosides and simple glycosides from the linseed meal. Fitoterapia. 2015 Oct;106:78-83. doi: 10.1016/j.fitote.2015.08.008. Epub 2015 Aug 22. PubMed PMID: 26307006.