Laetrile

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

MedKoo CAT#: 598230

CAS#: 1332-94-1

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


Chemical Structure

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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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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

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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.

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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.