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MedKoo Cat#: 525973 | Name: Levoglucosenone
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Description:

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

Levoglucosenone is a cytotoxic, against human hepatocarcinoma cell lines.

Chemical Structure

Levoglucosenone
CAS#37112-31-5

Theoretical Analysis

MedKoo Cat#: 525973

Name: Levoglucosenone

CAS#: 37112-31-5

Chemical Formula: C6H6O3

Exact Mass: 126.0317

Molecular Weight: 126.11

Elemental Analysis: C, 57.14; H, 4.80; O, 38.06

Price and Availability

Size Price Availability Quantity
200mg USD 350.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Levoglucosenone
IUPAC/Chemical Name
(1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
InChi Key
HITOXZPZGPXYHY-UJURSFKZSA-N
InChi Code
InChI=1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4-,6+/m0/s1
SMILES Code
O=C1C=C[C@@]2([H])CO[C@]1([H])O2
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
>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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levoglucosenone is a cytotoxic, against human hepatocarcinoma cell lines.
In vitro activity:
This study reports the cytotoxic effect of levoglucosenone and some related derivatives against hepatocarcinoma cell lines. Compounds were obtained in only one synthetic step and one of them showed an activity within the range of IC50 values of cisplatin, a frequently administered chemotherapy drug. Reference: Bioorg Med Chem Lett. 2016 Aug 15;26(16):3955-7. https://pubmed.ncbi.nlm.nih.gov/27422336/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 126.11 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
Formulation protocol:
1. Giri GF, Danielli M, Marinelli RA, Spanevello RA. Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines. Bioorg Med Chem Lett. 2016 Aug 15;26(16):3955-7. doi: 10.1016/j.bmcl.2016.07.007. Epub 2016 Jul 4. PMID: 27422336.
In vitro protocol:
1. Giri GF, Danielli M, Marinelli RA, Spanevello RA. Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines. Bioorg Med Chem Lett. 2016 Aug 15;26(16):3955-7. doi: 10.1016/j.bmcl.2016.07.007. Epub 2016 Jul 4. PMID: 27422336.
In vivo protocol:
TBD
1: Sarnik J, Czubatka-Bienkowska A, Macieja A, Bielski R, Witczak ZJ, Poplawski T. The induction of oxidative stress in cervix carcinoma cells by levoglucosenone derived 4-S-salicyl derivative and (1-4)-S-thio-disaccharides. Part 4. Bioorg Med Chem Lett. 2017 Mar 1;27(5):1215-1219. doi: 10.1016/j.bmcl.2017.01.064. Epub 2017 Jan 22. PubMed PMID: 28185719. 2: Krishna SH, Walker TW, Dumesic JA, Huber GW. Kinetics of Levoglucosenone Isomerization. ChemSusChem. 2017 Jan 10;10(1):129-138. doi: 10.1002/cssc.201601308. Epub 2016 Dec 13. PubMed PMID: 27863100. 3: Alves Costa Pacheco A, Sherwood J, Zhenova A, McElroy CR, Hunt AJ, Parker HL, Farmer TJ, Constantinou A, De Bruyn M, Whitwood AC, Raverty W, Clark JH. Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives. ChemSusChem. 2016 Dec 20;9(24):3503-3512. doi: 10.1002/cssc.201600795. Epub 2016 Nov 17. PubMed PMID: 27860452. 4: Peru AA, Flourat AL, Gunawan C, Raverty W, Jevric M, Greatrex BW, Allais F. Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone. Molecules. 2016 Jul 29;21(8). pii: E988. doi: 10.3390/molecules21080988. PubMed PMID: 27483225. 5: Stockton KP, Greatrex BW. Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone. Org Biomol Chem. 2016 Aug 21;14(31):7520-8. doi: 10.1039/c6ob00933f. Epub 2016 Jul 18. PubMed PMID: 27424764. 6: Giri GF, Danielli M, Marinelli RA, Spanevello RA. Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines. Bioorg Med Chem Lett. 2016 Aug 15;26(16):3955-7. doi: 10.1016/j.bmcl.2016.07.007. Epub 2016 Jul 4. PubMed PMID: 27422336. 7: Teixeira AR, Flourat AL, Peru AA, Brunissen F, Allais F. Lipase-Catalyzed Baeyer-Villiger Oxidation of Cellulose-Derived Levoglucosenone into (S)-γ-Hydroxymethyl-α,β-Butenolide: Optimization by Response Surface Methodology. Front Chem. 2016 Apr 19;4:16. doi: 10.3389/fchem.2016.00016. eCollection 2016. PubMed PMID: 27148523; PubMed Central PMCID: PMC4835721. 8: Comba MB, Suárez AG, Sarotti AM, Mangione MI, Spanevello RA, Giordano ED. Synthesis of a 3-Thiomannoside. Org Lett. 2016 Apr 15;18(8):1748-51. doi: 10.1021/acs.orglett.6b00428. Epub 2016 Apr 7. PubMed PMID: 27053242. 9: Quah SY, Tan MS, Teh YH, Stanslas J. Pharmacological modulation of oncogenic Ras by natural products and their derivatives: Renewed hope in the discovery of novel anti-Ras drugs. Pharmacol Ther. 2016 Jun;162:35-57. doi: 10.1016/j.pharmthera.2016.03.010. Epub 2016 Mar 22. Review. PubMed PMID: 27016467. 10: Gerosa GG, Spanevello RA, Suárez AG, Sarotti AM. Joint Experimental, in Silico, and NMR Studies toward the Rational Design of Iminium-Based Organocatalyst Derived from Renewable Sources. J Org Chem. 2015 Aug 7;80(15):7626-34. doi: 10.1021/acs.joc.5b01214. Epub 2015 Jul 24. PubMed PMID: 26173931. 11: Casoni AI, Bidegain M, Cubitto MA, Curvetto N, Volpe MA. Pyrolysis of sunflower seed hulls for obtaining bio-oils. Bioresour Technol. 2015 Feb;177:406-9. doi: 10.1016/j.biortech.2014.11.105. Epub 2014 Dec 4. PubMed PMID: 25500616. 12: Zurita MA, Avila A, Spanevello RA, Suárez AG, Sarotti AM. Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone. Carbohydr Res. 2015 Jan 30;402:67-70. doi: 10.1016/j.carres.2014.07.019. Epub 2014 Aug 1. PubMed PMID: 25497334. 13: Lu Q, Ye XN, Zhang ZB, Dong CQ, Zhang Y. Catalytic fast pyrolysis of cellulose and biomass to produce levoglucosenone using magnetic SO4(2-)/TiO2-Fe3O4. Bioresour Technol. 2014 Nov;171:10-15. doi: 10.1016/j.biortech.2014.08.075. Epub 2014 Aug 23. PubMed PMID: 25173471. 14: Sarotti AM. Theoretical insight into the pyrolytic deformylation of levoglucosenone and isolevoglucosenone. Carbohydr Res. 2014 May 22;390:76-80. doi: 10.1016/j.carres.2014.03.017. Epub 2014 Mar 22. PubMed PMID: 24747557. 15: Ostermeier M, Schobert R. Total synthesis of (+)-chloriolide. J Org Chem. 2014 May 2;79(9):4038-42. doi: 10.1021/jo500527g. Epub 2014 Apr 15. PubMed PMID: 24708255. 16: Giordano ED, Frinchaboy A, Suárez AG, Spanevello RA. Synthesis of tri-O-acetyl-D-allal from levoglucosenone. Org Lett. 2012 Sep 7;14(17):4602-5. doi: 10.1021/ol302061a. Epub 2012 Aug 24. PubMed PMID: 22920651. 17: Sarotti AM, Spanevello RA, Suárez AG, Echeverría GA, Piro OE. 1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development. Org Lett. 2012 May 18;14(10):2556-9. doi: 10.1021/ol3008588. Epub 2012 Apr 30. PubMed PMID: 22545814. 18: Wang S, Guo X, Liang T, Zhou Y, Luo Z. Mechanism research on cellulose pyrolysis by Py-GC/MS and subsequent density functional theory studies. Bioresour Technol. 2012 Jan;104:722-8. doi: 10.1016/j.biortech.2011.10.078. Epub 2011 Oct 30. PubMed PMID: 22100230. 19: Sui XW, Wang Z, Liao B, Zhang Y, Guo QX. Preparation of levoglucosenone through sulfuric acid promoted pyrolysis of bagasse at low temperature. Bioresour Technol. 2012 Jan;103(1):466-9. doi: 10.1016/j.biortech.2011.10.010. Epub 2011 Oct 12. PubMed PMID: 22047659. 20: Wang Z, Lu Q, Zhu XF, Zhang Y. Catalytic fast pyrolysis of cellulose to prepare levoglucosenone using sulfated zirconia. ChemSusChem. 2011 Jan 17;4(1):79-84. doi: 10.1002/cssc.201000210. Epub 2010 Nov 12. PubMed PMID: 21226215.

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