l-Limonene | CAS#5989-54-8 | antimicrobial

MedKoo Cat#: 597485 | Name: l-Limonene

Featured

Description:

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

l-Limonene is a monoterpenoid compound, and is mostly used in perfumery and in flavoring. On irradiation, it undergoes radiolysis, which leads to a reduction in the optical purity. l-Limonene also shows potent antimicrobial activity.

Chemical Structure

l-Limonene

CAS#5989-54-8

Theoretical Analysis

MedKoo Cat#: 597485

Name: l-Limonene

CAS#: 5989-54-8

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
50g	USD 350.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

l-Limonene; (S)-Limonene; beta-Limonene; AI3-25390;

IUPAC/Chemical Name

(S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

InChi Key

XMGQYMWWDOXHJM-SNVBAGLBSA-N

InChi Code

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1

SMILES Code

CC1=CC[C@@H](C(C)=C)CC1

Appearance

Liquid

Purity

>96% (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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape.

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	734.01
	Water	50.0	367.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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: Hajagos-Tóth J, Hódi Á, Seres AB, Gáspár R. Effects of d- and l-limonene on the pregnant rat myometrium in vitro. Croat Med J. 2015 Oct;56(5):431-8. PubMed PMID: 26526880; PubMed Central PMCID: PMC4655928. 2: Zhang CF, Yang ZL, Luo JB. [Effects of D-limonene and L-limonene on transdermal absorption of ligustrazine hydrochloride]. Yao Xue Xue Bao. 2006 Aug;41(8):772-7. Chinese. PubMed PMID: 17039786. 3: Kristiansen E, Madsen C. Induction of protein droplet (alpha 2 mu-globulin) nephropathy in male rats after short-term dosage with 1,8-cineole and l-limonene. Toxicol Lett. 1995 Oct;80(1-3):147-52. PubMed PMID: 7482582. 4: Chung IM, Seo SH, Kang EY, Park WH, Moon HI. Larvicidal effects of the major essential oil of Pittosporum tobira against Aedes aegypti (L.). J Enzyme Inhib Med Chem. 2010 Jun;25(3):391-3. doi: 10.3109/14756360903185952. Retraction in: J Enzyme Inhib Med Chem. 2012 Oct;27(5):758. PubMed PMID: 19874194. 5: Maruyama T, Ito M, Kiuchi F, Honda G. Molecular cloning, functional expression and characterization of d-limonene synthase from Schizonepeta tenuifolia. Biol Pharm Bull. 2001 Apr;24(4):373-7. PubMed PMID: 11305598. 6: Deweer C, Yaguiyan A, Muchembled J, Sahmer K, Dermont C, Halama P. In vitro evaluation of dill seed essential oil antifungal activities to control Zymoseptoria tritici. Commun Agric Appl Biol Sci. 2013;78(3):489-95. PubMed PMID: 25151824. 7: Chen J, Lu M, Jing Y, Dong J. The synthesis of L-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. Bioorg Med Chem. 2006 Oct 1;14(19):6539-47. Epub 2006 Jun 27. PubMed PMID: 16806947. 8: Foti C, Zambonin CG, Conserva A, Casulli C, D'Accolti L, Angelini G. Occupational contact dermatitis to a limonene-based solvent in a histopathology technician. Contact Dermatitis. 2007 Feb;56(2):109-12. PubMed PMID: 17244081. 9: Maruyama T, Saeki D, Ito M, Honda G. Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa. Biol Pharm Bull. 2002 May;25(5):661-5. PubMed PMID: 12033511. 10: Cal K, Janicki S, Sznitowska M. In vitro studies on penetration of terpenes from matrix-type transdermal systems through human skin. Int J Pharm. 2001 Aug 14;224(1-2):81-8. PubMed PMID: 11472817. 11: Zhang CF, Yang ZL, Luo JB. Effects of enantiomer and isomer permeation enhancers on transdermal delivery of ligustrazine hydrochloride. Pharm Dev Technol. 2006;11(4):417-24. PubMed PMID: 17101512. 12: Şanli A, Karadoğan T. GEOGRAPHICAL IMPACT ON ESSENTIAL OIL COMPOSITION OF ENDEMIC KUNDMANNIA ANATOLICA HUB.-MOR. (APIACEAE). Afr J Tradit Complement Altern Med. 2016 Nov 23;14(1):131-137. doi: 10.21010/ajtcam.v14i1.14. eCollection 2017. PubMed PMID: 28480390; PubMed Central PMCID: PMC5411863. 13: Kumar P, Singh SK, Mishra DN, Girotra P. Enhancement of ketorolac tromethamine permeability through rat skin using penetration enhancers: An ex-vivo study. Int J Pharm Investig. 2015 Jul-Sep;5(3):142-6. doi: 10.4103/2230-973X.160850. PubMed PMID: 26258055; PubMed Central PMCID: PMC4522863. 14: Jitviriyanon S, Phanthong P, Lomarat P, Bunyapraphatsara N, Porntrakulpipat S, Paraksa N. In vitro study of anti-coccidial activity of essential oils from indigenous plants against Eimeria tenella. Vet Parasitol. 2016 Sep 15;228:96-102. doi: 10.1016/j.vetpar.2016.08.020. Epub 2016 Aug 28. PubMed PMID: 27692340. 15: Kim MJ, Yang KW, Kim SS, Park SM, Park KJ, Kim KS, Choi YH, Cho KK, Hyun CG. Chemical composition and anti-inflammation activity of essential oils from Citrus unshiu flower. Nat Prod Commun. 2014 May;9(5):727-30. PubMed PMID: 25026734. 16: van Beilen JB, Holtackers R, Lüscher D, Bauer U, Witholt B, Duetz WA. Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putida. Appl Environ Microbiol. 2005 Apr;71(4):1737-44. PubMed PMID: 15811996; PubMed Central PMCID: PMC1082528. 17: Surratt JD, Gómez-González Y, Chan AW, Vermeylen R, Shahgholi M, Kleindienst TE, Edney EO, Offenberg JH, Lewandowski M, Jaoui M, Maenhaut W, Claeys M, Flagan RC, Seinfeld JH. Organosulfate formation in biogenic secondary organic aerosol. J Phys Chem A. 2008 Sep 11;112(36):8345-78. doi: 10.1021/jp802310p. Epub 2008 Aug 19. PubMed PMID: 18710205. 18: Kim MJ, Yang KW, Kim SS, Park SM, Park KJ, Kim KS, Choi YH, Cho KK, Lee NH, Hyun CG. Chemical composition and anti-inflammatory effects of essential oil from Hallabong flower. EXCLI J. 2013 Nov 7;12:933-42. eCollection 2013. PubMed PMID: 27366141; PubMed Central PMCID: PMC4928015. 19: Clarin T, Sandhu S, Apfelbach R. Odor detection and odor discrimination in subadult and adult rats for two enantiomeric odorants supported by c-fos data. Behav Brain Res. 2010 Jan 20;206(2):229-35. doi: 10.1016/j.bbr.2009.09.022. Epub 2009 Sep 17. PubMed PMID: 19766144. 20: Mohamad RH, El-Bastawesy AM, Abdel-Monem MG, Noor AM, Al-Mehdar HA, Sharawy SM, El-Merzabani MM. Antioxidant and anticarcinogenic effects of methanolic extract and volatile oil of fennel seeds (Foeniculum vulgare). J Med Food. 2011 Sep;14(9):986-1001. doi: 10.1089/jmf.2008.0255. Epub 2011 Aug 3. PubMed PMID: 21812646.