(d)-Limonene | CAS#5989-27-5 | cell cycle arrest | apoptosis

(d)-Limonene
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540267

CAS#: 5989-27-5

Description: (d)-Limonene is a commercial flavorant, odorant, cleaning solvent, and insecticide found in the rind of various citrus plants. It displays a wide range of activities, including cell cycle arrest and apoptosis in gastric carcinoma cells, inducing phase II enzyme expression to limit oxidative damage, and suppressing cytokine production by CD4+ and CD8+ T cells.

Chemical Structure

(d)-Limonene

CAS# 5989-27-5

Instruction

Theoretical Analysis

MedKoo Cat#: 540267
Name: (d)-Limonene
CAS#: 5989-27-5
Chemical Formula: C10H16
Exact Mass: 136.13
Molecular Weight: 136.230
Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (d)-Limonene; Carvene; Citrene; Kautschiin

IUPAC/Chemical Name: (R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

InChi Key: XMGQYMWWDOXHJM-JTQLQIEISA-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-/m0/s1

SMILES Code: C=C([C@H]1CC=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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 136.23 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:
In vitro protocol:
In vivo protocol:

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1: Sun J. D-Limonene: safety and clinical applications. Altern Med Rev. 2007 Sep;12(3):259-64. Review. PubMed PMID: 18072821.

2: Bei W, Zhou Y, Xing X, Zahi MR, Li Y, Yuan Q, Liang H. Organogel-nanoemulsion containing nisin and D-limonene and its antimicrobial activity. Front Microbiol. 2015 Sep 22;6:1010. doi: 10.3389/fmicb.2015.01010. eCollection 2015. PubMed PMID: 26441935; PubMed Central PMCID: PMC4585035.

3: Yang J, Jiang W, Guan B, Qiu X, Lu Y. Preparation of D-limonene oil-in-water nanoemulsion from an optimum formulation. J Oleo Sci. 2014;63(11):1133-40. Epub 2014 Oct 7. PubMed PMID: 25296572.

4: Rodríguez A, Shimada T, Cervera M, Redondo A, Alquézar B, Rodrigo MJ, Zacarías L, Palou L, López MM, Peña L. Resistance to pathogens in terpene down-regulated orange fruits inversely correlates with the accumulation of D-limonene in peel oil glands. Plant Signal Behav. 2015;10(6):e1028704. doi: 10.1080/15592324.2015.1028704. PubMed PMID: 26023857; PubMed Central PMCID: PMC4622707.

5: 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.

6: Zhang Z, Vriesekoop F, Yuan Q, Liang H. Effects of nisin on the antimicrobial activity of d-limonene and its nanoemulsion. Food Chem. 2014 May 1;150:307-12. doi: 10.1016/j.foodchem.2013.10.160. Epub 2013 Nov 12. PubMed PMID: 24360455.

7: Kim YW, Kim MJ, Chung BY, Bang du Y, Lim SK, Choi SM, Lim DS, Cho MC, Yoon K, Kim HS, Kim KB, Kim YS, Kwack SJ, Lee BM. Safety evaluation and risk assessment of d-Limonene. J Toxicol Environ Health B Crit Rev. 2013;16(1):17-38. doi: 10.1080/10937404.2013.769418. Review. PubMed PMID: 23573938.

8: Lu WC, Zhang TJ, Huang DW, Li PH. Nanoemulsion of D-limonene in water system prepared by ultrasonic emulsification. J Cosmet Sci. 2014 Jul-Aug;65(4):245-52. PubMed PMID: 25423744.

9: Zahi MR, Wan P, Liang H, Yuan Q. Formation and stability of D-limonene organogel-based nanoemulsion prepared by a high-pressure homogenizer. J Agric Food Chem. 2014 Dec 31;62(52):12563-9. doi: 10.1021/jf5032108. Epub 2014 Dec 16. PubMed PMID: 25514199.

10: Liu J, Zhu Y, Du G, Zhou J, Chen J. Response of Saccharomyces cerevisiae to D-limonene-induced oxidative stress. Appl Microbiol Biotechnol. 2013 Jul;97(14):6467-75. doi: 10.1007/s00253-013-4931-9. Epub 2013 May 5. PubMed PMID: 23644769.

11: Api AM, Ritacco G, Hawkins DR. The fate of dermally applied [14C]d-limonene in rats and humans. Int J Toxicol. 2013 Mar-Apr;32(2):130-5. doi: 10.1177/1091581813479979. Epub 2013 Mar 14. PubMed PMID: 23493903.

12: Pesonen M, Suomela S, Kuuliala O, Henriks-Eckerman ML, Aalto-Korte K. Occupational contact dermatitis caused by D-limonene. Contact Dermatitis. 2014 Nov;71(5):273-9. doi: 10.1111/cod.12287. Epub 2014 Aug 21. PubMed PMID: 25141986.

13: d'Alessio PA, Bisson JF, Béné MC. Anti-stress effects of d-limonene and its metabolite perillyl alcohol. Rejuvenation Res. 2014 Apr;17(2):145-9. doi: 10.1089/rej.2013.1515. Epub 2014 Apr 8. PubMed PMID: 24125633.

14: Wen C, Yuan Q, Liang H, Vriesekoop F. Preparation and stabilization of D-limonene Pickering emulsions by cellulose nanocrystals. Carbohydr Polym. 2014 Nov 4;112:695-700. doi: 10.1016/j.carbpol.2014.06.051. Epub 2014 Jun 27. PubMed PMID: 25129799.

15: Zhang XZ, Wang L, Liu DW, Tang GY, Zhang HY. Synergistic inhibitory effect of berberine and d-limonene on human gastric carcinoma cell line MGC803. J Med Food. 2014 Sep;17(9):955-62. doi: 10.1089/jmf.2013.2967. Epub 2014 Jul 21. PubMed PMID: 25045784; PubMed Central PMCID: PMC4152785.

16: Rehman MU, Tahir M, Khan AQ, Khan R, Oday-O-Hamiza, Lateef A, Hassan SK, Rashid S, Ali N, Zeeshan M, Sultana S. D-limonene suppresses doxorubicin-induced oxidative stress and inflammation via repression of COX-2, iNOS, and NFκB in kidneys of Wistar rats. Exp Biol Med (Maywood). 2014 Apr;239(4):465-76. doi: 10.1177/1535370213520112. Epub 2014 Feb 28. PubMed PMID: 24586096.

17: Jia SS, Xi GP, Zhang M, Chen YB, Lei B, Dong XS, Yang YM. Induction of apoptosis by D-limonene is mediated by inactivation of Akt in LS174T human colon cancer cells. Oncol Rep. 2013 Jan;29(1):349-54. doi: 10.3892/or.2012.2093. Epub 2012 Oct 19. PubMed PMID: 23117412.

18: d'Alessio PA, Mirshahi M, Bisson JF, Bene MC. Skin repair properties of d-Limonene and perillyl alcohol in murine models. Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):29-35. PubMed PMID: 24160248.

19: d'Alessio PA, Ostan R, Bisson JF, Schulzke JD, Ursini MV, Béné MC. Oral administration of d-limonene controls inflammation in rat colitis and displays anti-inflammatory properties as diet supplementation in humans. Life Sci. 2013 Jul 10;92(24-26):1151-6. doi: 10.1016/j.lfs.2013.04.013. Epub 2013 May 7. PubMed PMID: 23665426.

20: Jing L, Zhang Y, Fan S, Gu M, Guan Y, Lu X, Huang C, Zhou Z. Preventive and ameliorating effects of citrus D-limonene on dyslipidemia and hyperglycemia in mice with high-fat diet-induced obesity. Eur J Pharmacol. 2013 Sep 5;715(1-3):46-55. doi: 10.1016/j.ejphar.2013.06.022. Epub 2013 Jul 6. PubMed PMID: 23838456.

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