Synonym
Xyloidone; NSC 106453; NSC-106453; NSC106453; NSC 629748.
IUPAC/Chemical Name
2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl- (8CI)(9CI)
InChi Key
OWFHAMHRUCUSRM-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3
SMILES Code
O=C(C1=C2OC(C)(C)C=C1)C3=C(C2=O)C=CC=C3
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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
240.26
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 |
1: Moraes DC, Curvelo JAR, Anjos CA, Moura KCG, Pinto MCFR, Portela MB, Soares RMA. β-lapachone and α-nor-lapachone modulate Candida albicans viability and virulence factors. J Mycol Med. 2018 Mar 26. pii: S1156-5233(17)30379-7. doi: 10.1016/j.mycmed.2018.03.004. [Epub ahead of print] PubMed PMID: 29598974.
2: Oliveira Silva E, Cruz de Carvalho T, Parshikov IA, Alves dos Santos R, Silva Emery F, Jacometti Cardoso Furtado NA. Cytotoxicity of lapachol metabolites produced by probiotics. Lett Appl Microbiol. 2014 Jul;59(1):108-14. doi: 10.1111/lam.12251. Epub 2014 Apr 9. PubMed PMID: 24635204.
3: Garkavtsev I, Chauhan VP, Wong HK, Mukhopadhyay A, Glicksman MA, Peterson RT, Jain RK. Dehydro-alpha-lapachone, a plant product with antivascular activity. Proc Natl Acad Sci U S A. 2011 Jul 12;108(28):11596-601. doi: 10.1073/pnas.1104225108. Epub 2011 Jun 27. PubMed PMID: 21709229; PubMed Central PMCID: PMC3136298.
4: Nasiri HR, Bolte M, Schwalbe H. Electrochemical and crystal structural analysis of alpha- and dehydro-alpha-lapachones. Nat Prod Res. 2008;22(14):1225-1230. doi: 10.1080/14786410701654925. PubMed PMID: 18932085.
5: Cho JY, Kim HY, Choi GJ, Jang KS, Lim HK, Lim CH, Cho KY, Kim JC. Dehydro-alpha-lapachone isolated from Catalpa ovata stems: activity against plant pathogenic fungi. Pest Manag Sci. 2006 May;62(5):414-8. PubMed PMID: 16550502.
6: Müller K, Sellmer A, Wiegrebe W. Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth. J Nat Prod. 1999 Aug;62(8):1134-6. PubMed PMID: 10479319.
7: Pinto AV, Ferreira VF, Coutada LC. [Synthesis of xyloidone and lapachone analogs]. An Acad Bras Cienc. 1980 Sep;52(3):477-9. Portuguese. PubMed PMID: 7011134.
