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MedKoo Cat#: 596471 | Name: Limonene oxide, (-)-

Description:

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

Limonene oxide, (-)- is a bioactive chemical.

Chemical Structure

Limonene oxide, (-)-
Limonene oxide, (-)-
CAS#203719-53-3

Theoretical Analysis

MedKoo Cat#: 596471

Name: Limonene oxide, (-)-

CAS#: 203719-53-3

Chemical Formula: C10H16O

Exact Mass: 152.1201

Molecular Weight: 152.24

Elemental Analysis: C, 78.90; H, 10.59; O, 10.51

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Synonym
Limonene oxide, (-)-; FEMA No. 4656; L-1,2-Epoxylimonene;
IUPAC/Chemical Name
(4S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
InChi Key
CCEFMUBVSUDRLG-IDKOKCKLSA-N
InChi Code
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m0/s1
SMILES Code
CC([C@H]1CCC2(C)C(O2)C1)=C
Appearance
To be determined
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:
Limonene oxide, (-)- is a bioactive chemical.
In vitro activity:
(+)-Limonene oxide was more effective in killing these parasites than α-terpinene, with 86 and 90% mortality at concentrations of 36 and 55.4 mg/L, respectively, with a 5-h treatment. The estimated 5-h EC50 of (+)-limonene oxide was 4.8 mg/L. Reference: J Parasit Dis. 2019 Dec;43(4):739-742. https://pubmed.ncbi.nlm.nih.gov/31749549/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 152.24 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. Morales-Serna FN, Caña-Bozada VH, López-Moreno DG, Medina-Guerrero RM, Morales-Serna JA, Fajer-Ávila EJ. In vitro efficacy of two terpenes against ancyrocephalid monogeneans from Nile tilapia. J Parasit Dis. 2019 Dec;43(4):739-742. doi: 10.1007/s12639-019-01150-2. Epub 2019 Aug 19. PMID: 31749549; PMCID: PMC6841818.
In vitro protocol:
1. Morales-Serna FN, Caña-Bozada VH, López-Moreno DG, Medina-Guerrero RM, Morales-Serna JA, Fajer-Ávila EJ. In vitro efficacy of two terpenes against ancyrocephalid monogeneans from Nile tilapia. J Parasit Dis. 2019 Dec;43(4):739-742. doi: 10.1007/s12639-019-01150-2. Epub 2019 Aug 19. PMID: 31749549; PMCID: PMC6841818.
In vivo protocol:
TBD
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[Epub ahead of print] PubMed PMID: 29463326. 5: Chueca B, Renzoni A, Berdejo D, Pagán R, Kelley WL, García-Gonzalo D. Whole-Genome Sequencing and Genetic Analysis Reveal Novel Stress Responses to Individual Constituents of Essential Oils in Escherichia coli. Appl Environ Microbiol. 2018 Mar 19;84(7). pii: e02538-17. doi: 10.1128/AEM.02538-17. Print 2018 Apr 1. PubMed PMID: 29374037; PubMed Central PMCID: PMC5861813. 6: Ciriminna R, Parrino F, De Pasquale C, Palmisano L, Pagliaro M. Photocatalytic partial oxidation of limonene to 1,2 limonene oxide. Chem Commun (Camb). 2018 Jan 23;54(8):1008-1011. doi: 10.1039/c7cc09788c. PubMed PMID: 29323370. 7: Cortés DA, Elrod MJ. Kinetics of the Aqueous Phase Reactions of Atmospherically Relevant Monoterpene Epoxides. J Phys Chem A. 2017 Dec 7;121(48):9297-9305. doi: 10.1021/acs.jpca.7b09427. Epub 2017 Nov 27. PubMed PMID: 29148753. 8: Reiter M, Vagin S, Kronast A, Jandl C, Rieger B. A Lewis acid β-diiminato-zinc-complex as all-rounder for co- and terpolymerisation of various epoxides with carbon dioxide. Chem Sci. 2017 Mar 1;8(3):1876-1882. doi: 10.1039/c6sc04477h. Epub 2016 Nov 17. PubMed PMID: 28567266; PubMed Central PMCID: PMC5444112. 9: Lee JY, Jo WK. Application of ultrasound-aided method for the synthesis of CdS-incorporated three-dimensional TiO(2) photocatalysts with enhanced performance. Ultrason Sonochem. 2017 Mar;35(Pt A):440-448. doi: 10.1016/j.ultsonch.2016.10.023. Epub 2016 Oct 21. PubMed PMID: 28340948. 10: Rinaldi S, Gori A, Annovazzi C, Ferrandi EE, Monti D, Colombo G. Unraveling Energy and Dynamics Determinants to Interpret Protein Functional Plasticity: The Limonene-1,2-epoxide-hydrolase Case Study. J Chem Inf Model. 2017 Apr 24;57(4):717-725. doi: 10.1021/acs.jcim.6b00504. Epub 2017 Mar 29. PubMed PMID: 28298080. 11: de Almeida AA, Silva RO, Nicolau LA, de Brito TV, de Sousa DP, Barbosa AL, de Freitas RM, Lopes LD, Medeiros JR, Ferreira PM. Physio-pharmacological Investigations About the Anti-inflammatory and Antinociceptive Efficacy of (+)-Limonene Epoxide. Inflammation. 2017 Apr;40(2):511-522. doi: 10.1007/s10753-016-0496-y. PubMed PMID: 28091830. 12: Pellegrini MC, Alonso-Salces RM, Umpierrez ML, Rossini C, Fuselli SR. Chemical Composition, Antimicrobial Activity, and Mode of Action of Essential Oils against Paenibacillus larvae, Etiological Agent of American Foulbrood on Apis mellifera. Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600382. Epub 2017 Mar 20. PubMed PMID: 27943550. 13: Lederer MR, Staniec AR, Coates Fuentes ZL, Van Ry DA, Hinrichs RZ. Heterogeneous Reactions of Limonene on Mineral Dust: Impacts of Adsorbed Water and Nitric Acid. J Phys Chem A. 2016 Dec 8;120(48):9545-9556. Epub 2016 Nov 21. PubMed PMID: 27933906. 14: Loru D, Quesada-Moreno MM, Avilés-Moreno JR, Jarman N, Huet TR, López-González JJ, Sanz ME. Conformational Flexibility of Limonene Oxide Studied By Microwave Spectroscopy. Chemphyschem. 2017 Feb 2;18(3):274-280. doi: 10.1002/cphc.201600991. Epub 2016 Dec 23. PubMed PMID: 27880857. 15: Muhammad F, Jaberi-Douraki M, de Sousa DP, Riviere JE. Modulation of chemical dermal absorption by 14 natural products: a quantitative structure permeation analysis of components often found in topical preparations. Cutan Ocul Toxicol. 2017 Sep;36(3):237-252. doi: 10.1080/15569527.2016.1258709. Epub 2016 Dec 14. PubMed PMID: 27825281. 16: Lipsa D, Leva P, Barrero-Moreno J, Coelhan M. Inflammatory effects induced by selected limonene oxidation products: 4-OPA, IPOH, 4-AMCH in human bronchial (16HBE14o-) and alveolar (A549) epithelial cell lines. Toxicol Lett. 2016 Nov 16;262:70-79. doi: 10.1016/j.toxlet.2016.08.023. Epub 2016 Aug 27. PubMed PMID: 27575568. 17: Jaleta KT, Hill SR, Birgersson G, Tekie H, Ignell R. Chicken volatiles repel host-seeking malaria mosquitoes. Malar J. 2016 Jul 21;15(1):354. doi: 10.1186/s12936-016-1386-3. PubMed PMID: 27439360; PubMed Central PMCID: PMC4955153. 18: Hauenstein O, Agarwal S, Greiner A. Bio-based polycarbonate as synthetic toolbox. Nat Commun. 2016 Jun 15;7:11862. doi: 10.1038/ncomms11862. PubMed PMID: 27302694; PubMed Central PMCID: PMC4912624. 19: Chueca B, Berdejo D, Gomes-Neto NJ, Pagán R, García-Gonzalo D. Emergence of Hyper-Resistant Escherichia coli MG1655 Derivative Strains after Applying Sub-Inhibitory Doses of Individual Constituents of Essential Oils. Front Microbiol. 2016 Mar 4;7:273. doi: 10.3389/fmicb.2016.00273. eCollection 2016. PubMed PMID: 26973641; PubMed Central PMCID: PMC4777736. 20: Andrade LN, Lima TC, Amaral RG, Pessoa Cdo Ó, Filho MO, Soares BM, Nascimento LG, Carvalho AA, de Sousa DP. Evaluation of the cytotoxicity of structurally correlated p-menthane derivatives. Molecules. 2015 Jul 21;20(7):13264-80. doi: 10.3390/molecules200713264. PubMed PMID: 26197313.