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MedKoo Cat#: 591691 | Name: Limonene
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Description:

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

Limonene is a colorless liquid with a citrus-like odor; found in large number of oils; the most common terpene and is produced by hundreds of plants; dissolving agent for gall stones & gutta-percha; used in surfactant as a penetration enhancer.

Chemical Structure

Limonene
Limonene
CAS#138-86-3

Theoretical Analysis

MedKoo Cat#: 591691

Name: Limonene

CAS#: 138-86-3

Chemical Formula: C10H16

Exact Mass: 136.1252

Molecular Weight: 136.24

Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

Size Price Availability Quantity
25mL USD 250.00 2 Weeks
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Synonym
Limonene; NSC 21446; NSC-21446; NSC21446; (±)-Limonene; DL-Limonene
IUPAC/Chemical Name
Cyclohexene, 1-methyl-4-(1-methylethenyl)-
InChi Key
XMGQYMWWDOXHJM-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
SMILES Code
C=C(C1CC=C(C)CC1)C
Appearance
Liquid
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 is a monoterpene in citrus peel oil.
In vitro activity:
In the present study, the effect of limonene on normal lymphocytes proliferation and its relation with H(2)O(2) level modulation was analysed, evaluating its effect on the activity of cell antioxidant enzymes, such as catalase, peroxidase and superoxide dismutase. Limonene exerted a biphasic effect on cell proliferation; the increase in cell proliferation was related to the decrease in H(2)O(2) level by the increase in catalase and peroxidase activities. Reference: Basic Clin Pharmacol Toxicol. 2010 Jan;106(1):38-44. https://pubmed.ncbi.nlm.nih.gov/19796276/
In vivo activity:
Male Wistar rats were orally treated with vehicle (8% tween 80), carbenoxolone (100 mg/kg) or limonene (25, 50 or 100 mg/kg) and then orally received ethanol to induce gastric ulcers formation. These results showed that limonene 50 mg/kg was the lowest effective dose, offering 93% of reduction in gastric ulcer area compared with the vehicle. Limonene displayed anti-inflammatory activity through decreasing the levels of TNF-a, IL-6, and IL-1β and increasing the level of IL-10. Limonene could down-regulate the expression of Nf-κb, Il-1β, and Mpo and up-regulate the expression of Gpx. Reference: Phytomedicine. 2019 Feb;53:37-42. https://pubmed.ncbi.nlm.nih.gov/30668410/

Preparing Stock Solutions

The following data is based on the product molecular weight 136.24 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. Zhu T, Li Y, Feng T, Yang Y, Zhang K, Gao J, Quan X, Qian Y, Yu H, Qian B. D-Limonene inhibits the occurrence and progression of LUAD through suppressing lipid droplet accumulation induced by PM2.5 exposure in vivo and in vitro. Respir Res. 2022 Dec 10;23(1):338. doi: 10.1186/s12931-022-02270-9. PMID: 36496421; PMCID: PMC9741803. 2. Roberto D, Micucci P, Sebastian T, Graciela F, Anesini C. Antioxidant activity of limonene on normal murine lymphocytes: relation to H2O2 modulation and cell proliferation. Basic Clin Pharmacol Toxicol. 2010 Jan;106(1):38-44. doi: 10.1111/j.1742-7843.2009.00467.x. Epub 2009 Oct 1. PMID: 19796276. 3. de Souza MC, Vieira AJ, Beserra FP, Pellizzon CH, Nóbrega RH, Rozza AL. Gastroprotective effect of limonene in rats: Influence on oxidative stress, inflammation and gene expression. Phytomedicine. 2019 Feb;53:37-42. doi: 10.1016/j.phymed.2018.09.027. Epub 2018 Sep 4. PMID: 30668410. 4. Chi G, Wei M, Xie X, Soromou LW, Liu F, Zhao S. Suppression of MAPK and NF-κB pathways by limonene contributes to attenuation of lipopolysaccharide-induced inflammatory responses in acute lung injury. Inflammation. 2013 Apr;36(2):501-11. doi: 10.1007/s10753-012-9571-1. Erratum in: Inflammation. 2013 Aug;36(4):982. PMID: 23180366.
In vitro protocol:
1. Zhu T, Li Y, Feng T, Yang Y, Zhang K, Gao J, Quan X, Qian Y, Yu H, Qian B. D-Limonene inhibits the occurrence and progression of LUAD through suppressing lipid droplet accumulation induced by PM2.5 exposure in vivo and in vitro. Respir Res. 2022 Dec 10;23(1):338. doi: 10.1186/s12931-022-02270-9. PMID: 36496421; PMCID: PMC9741803. 2. Roberto D, Micucci P, Sebastian T, Graciela F, Anesini C. Antioxidant activity of limonene on normal murine lymphocytes: relation to H2O2 modulation and cell proliferation. Basic Clin Pharmacol Toxicol. 2010 Jan;106(1):38-44. doi: 10.1111/j.1742-7843.2009.00467.x. Epub 2009 Oct 1. PMID: 19796276.
In vivo protocol:
1. de Souza MC, Vieira AJ, Beserra FP, Pellizzon CH, Nóbrega RH, Rozza AL. Gastroprotective effect of limonene in rats: Influence on oxidative stress, inflammation and gene expression. Phytomedicine. 2019 Feb;53:37-42. doi: 10.1016/j.phymed.2018.09.027. Epub 2018 Sep 4. PMID: 30668410. 2. Chi G, Wei M, Xie X, Soromou LW, Liu F, Zhao S. Suppression of MAPK and NF-κB pathways by limonene contributes to attenuation of lipopolysaccharide-induced inflammatory responses in acute lung injury. Inflammation. 2013 Apr;36(2):501-11. doi: 10.1007/s10753-012-9571-1. Erratum in: Inflammation. 2013 Aug;36(4):982. PMID: 23180366.
1: Le TM, Csámpai A, Fülöp F, Szakonyi Z. Regio- and stereoselective synthesis of bicyclic limonene-based chiral aminodiols and spirooxazolidines. Chemistry. 2018 Jun 20. doi: 10.1002/chem.201802484. [Epub ahead of print] PubMed PMID: 29924432. 2: Plastina P, Apriantini A, Meijerink J, Witkamp R, Gabriele B, Fazio A. In Vitro Anti-Inflammatory and Radical Scavenging Properties of Chinotto (Citrus myrtifolia Raf.) Essential Oils. Nutrients. 2018 Jun 18;10(6). pii: E783. doi: 10.3390/nu10060783. PubMed PMID: 29912150. 3: Cardoso-Teixeira AC, Ferreira-da-Silva FW, Peixoto-Neves D, Oliveira-Abreu K, Pereira-Gonçalves Á, Coelho-de-Souza AN, Leal-Cardoso JH. Hydroxyl Group and Vasorelaxant Effects of Perillyl Alcohol, Carveol, Limonene on Aorta Smooth Muscle of Rats. Molecules. 2018 Jun 13;23(6). pii: E1430. doi: 10.3390/molecules23061430. PubMed PMID: 29899230. 4: Lemes RS, Alves CCF, Estevam EBB, Santiago MB, Martins CHG, Santos TCLD, Crotti AEM, Miranda MLD. Chemical composition and antibacterial activity of essential oils from Citrus aurantifolia leaves and fruit peel against oral pathogenic bacteria. An Acad Bras Cienc. 2018 Apr-Jun;90(2):1285-1292. doi: 10.1590/0001-3765201820170847. PubMed PMID: 29898096. 5: Baurès E, Blanchard O, Mercier F, Surget E, le Cann P, Rivier A, Gangneux JP, Florentin A. Indoor air quality in two French hospitals: Measurement of chemical and microbiological contaminants. Sci Total Environ. 2018 Jun 9;642:168-179. doi: 10.1016/j.scitotenv.2018.06.047. [Epub ahead of print] PubMed PMID: 29894876. 6: Qin Z, Zhang R, Yu J. [Perillyl alcohol production by engineered heterologous mevalonate pathway in Escherichia coli]. Sheng Wu Gong Cheng Xue Bao. 2018 May 25;34(5):722-730. doi: 10.13345/j.cjb.170472. Chinese. PubMed PMID: 29893080. 7: Qi D, Miao A, Cao J, Wang W, Chen W, Pang S, He X, Ma C. Study on the effects of rapid aging technology on the aroma quality of white tea using GC-MS combined with chemometrics: In comparison with natural aged and fresh white tea. Food Chem. 2018 Nov 1;265:189-199. doi: 10.1016/j.foodchem.2018.05.080. Epub 2018 May 18. PubMed PMID: 29884372. 8: Koubaa FG, Abdennabi R, Soussi Ben Salah A, El Feki A. Microwave extraction of Salvia officinalis essential oil and assessment of its GC-MS identification and protective effects versus vanadium-induced nephrotoxicity in Wistar rats models. Arch Physiol Biochem. 2018 Jun 8:1-10. doi: 10.1080/13813455.2018.1478427. [Epub ahead of print] PubMed PMID: 29884068. 9: Assier H, Tetart F, Avenel-Audran M, Barbaud A, Ferrier-le Bouëdec MC, Giordano-Labadie F, Milpied B, Amsler E, Collet E, Girardin P, Soria A, Waton J, Truchetet F, Bourrain JL, Gener G, Bernier C, Raison-Peyron N; Dermato-Allergology Group of the French Society of Dermatology (DAG). Is a specific eyelid patch test series useful? Results of a French prospective study. Contact Dermatitis. 2018 Jun 8. doi: 10.1111/cod.13040. [Epub ahead of print] PubMed PMID: 29882592. 10: da Silva LVF, Veras Mourão RH, Manimala J, Lnenicka GA. The essential oil of Lippia alba and its components affect Drosophila behavior and synaptic physiology. J Exp Biol. 2018 Jun 7. pii: jeb.176909. doi: 10.1242/jeb.176909. [Epub ahead of print] PubMed PMID: 29880632. 11: Dos Passos Menezes P, de Oliveira Araujo F, Andrade TA, Trindade IAS, de Araujo-Filho HG, de Souza Siqueira Quintans J, Quintans-Junior LJ, Costa EV, Menezes LRA, de Almeida RN, Braga RM, Serafini MR, de Souza Araujo AA. Physicochemical characterization and antinociceptive effect of β-cyclodextrin/Lippia pedunculosa essential oil in mice. Curr Top Med Chem. 2018 Jun 6. doi: 10.2174/1568026618666180607081742. [Epub ahead of print] PubMed PMID: 29875002. 12: Sonboli A, Mirzania F, Gholipour A. Essential oil composition of Dracocephalum kotschyi Boiss. from Iran. Nat Prod Res. 2018 Jun 6:1-4. doi: 10.1080/14786419.2018.1482550. [Epub ahead of print] PubMed PMID: 29873264. 13: Schrimpf A, Hempel F, Li A, Linne U, Maier UG, Reetz MT, Geyer A. Hinge-Type Dimerization of Proteins by a Tetracysteine Peptide of High Pairing Specificity. Biochemistry. 2018 Jun 14. doi: 10.1021/acs.biochem.8b00475. [Epub ahead of print] PubMed PMID: 29863338. 14: Suntar I, Khan H, Patel S, Celano R, Rastrelli L. An Overview on Citrus aurantium L.: Its Functions as Food Ingredient and Therapeutic Agent. Oxid Med Cell Longev. 2018 May 2;2018:7864269. doi: 10.1155/2018/7864269. eCollection 2018. Review. PubMed PMID: 29854097; PubMed Central PMCID: PMC5954905. 15: Cautela D, Vella FM, Castaldo D, Laratta B. Characterization of essential oil recovered from fennel horticultural wastes. Nat Prod Res. 2018 May 30:1-5. doi: 10.1080/14786419.2018.1478827. [Epub ahead of print] PubMed PMID: 29846092. 16: Saiki JP, Cao H, Van Wassenhove LD, Viswanathan V, Bloomstein J, Nambiar DK, Mattingly AJ, Jiang D, Chen CH, Stevens MC, Simmons AL, Park HS, von Eyben R, Kool ET, Sirjani D, Knox SM, Le QT, Mochly-Rosen D. Aldehyde dehydrogenase 3A1 activation prevents radiation-induced xerostomia by protecting salivary stem cells from toxic aldehydes. Proc Natl Acad Sci U S A. 2018 Jun 12;115(24):6279-6284. doi: 10.1073/pnas.1802184115. Epub 2018 May 24. PubMed PMID: 29794221; PubMed Central PMCID: PMC6004437. 17: Lee HR, Lee SC, Lee DH, Jung M, Kwon JH, Huh MJ, Kim DS, Lee JE, Park IK. Identification of Aggregation-Sex Pheromone of the Korean Monochamus alternatus (Coleoptera: Cerambycidae) Population, the Main Vector of Pine Wood Nematode. J Econ Entomol. 2018 May 19. doi: 10.1093/jee/toy137. [Epub ahead of print] PubMed PMID: 29788181. 18: Sawiak L, Bailes K, Harbottle D, Clegg PS. Mixing Time, Inversion and Multiple Emulsion Formation in a Limonene and Water Pickering Emulsion. Front Chem. 2018 May 4;6:132. doi: 10.3389/fchem.2018.00132. eCollection 2018. PubMed PMID: 29780799; PubMed Central PMCID: PMC5945812. 19: Chinthakunta N, Cheemanapalli S, Chinthakunta S, Anuradha CM, Chitta SK. A new insight into identification of in silico analysis of natural compounds targeting GPR120. Netw Model Anal Health Inform Bioinform. 2018;7(1):8. doi: 10.1007/s13721-018-0166-0. Epub 2018 May 14. PubMed PMID: 29780684; PubMed Central PMCID: PMC5951878. 20: Villa-Ruano N, Pacheco-Hernández Y, Becerra-Martínez E, Zárate-Reyes JA, Cruz-Durán R. Chemical profile and pharmacological effects of the resin and essential oil from Bursera slechtendalii: A medicinal "copal tree" of southern Mexico. Fitoterapia. 2018 Jul;128:86-92. doi: 10.1016/j.fitote.2018.05.009. Epub 2018 May 16. PubMed PMID: 29777752.