Eucalyptol | CAS#470-82-6

MedKoo Cat#: 329674 | Name: Eucalyptol

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Description:

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

Eucalyptol is a natural organic compound that is a colorless liquid. Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products and beverages. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is claimed that it is added to improve the flavor. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant, as well as an inactive ingredient in body powder.

Chemical Structure

Eucalyptol

CAS#470-82-6

Theoretical Analysis

MedKoo Cat#: 329674

Name: Eucalyptol

CAS#: 470-82-6

Chemical Formula: C10H18O

Exact Mass: 154.1358

Molecular Weight: 154.25

Elemental Analysis: C, 77.87; H, 11.76; O, 10.37

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00	2 Weeks
500mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Eucalyptol; Cineole; 1,8-Cineole; 1,8-Cineol; 1,8-epoxy-p-Menthane; NSC 6171; NSC6171; NSC-6171;

IUPAC/Chemical Name

1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane

InChi Key

WEEGYLXZBRQIMU-UHFFFAOYSA-N

InChi Code

InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3

SMILES Code

CC1(C)OC2(C)CCC1CC2

Appearance

Oily 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

It is a cyclic ether and a monoterpenoid. Eucalyptol is also known by a variety of synonyms: 1,8-cineol, 1,8-cineole, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole. In 1870, F. S. Cloez identified and ascribed the name eucalyptol to the dominant portion of Eucalyptus globulus oil.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

A bicyclic monoterpene with diverse biological activities.

In vitro activity:

The current study investigated that eucalyptol inhibited loss of RPE tight junction proteins under diabetic condition. The induction of the tight junction marker of ZO-1 was attenuated in RPE cells exposed to 33 mM glucose for 5 days in a temporal manner (Figure 1D). When 1–20 µM eucalyptol was added to glucose-loaded RPE cells for 4 days, the epithelial induction of ZO-1 and occludin-1 was highly reversed (Figure 1E). Reference: Antioxidants (Basel). 2020 Oct; 9(10): 1000. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7602655/

In vivo activity:

The effect of EUC (eucalyptol) administration on the formation of aortic lesions in normal and atherosclerotic rats is shown in Figure 1a-c. The atheromatous plaques and neointima were generated in the diabetic-atherosclerotic rats but the treatment inhibited the generation of any aortic lesions in the diabetic-atherosclerotic rats. Reference: Int J Prev Med. 2021; 12: 45. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8223915/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	129.66
	DMSO:PBS (pH 7.2) (1:4)	0.2	1.30
	DMF	20.0	129.66
	Ethanol	20.0	129.66

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 154.25 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. Kim DY, Kang MK, Lee EJ, Kim YH, Oh H, Kim SI, Oh SY, Na W, Kang YH. Eucalyptol Inhibits Amyloid-β-Induced Barrier Dysfunction in Glucose-Exposed Retinal Pigment Epithelial Cells and Diabetic Eyes. Antioxidants (Basel). 2020 Oct 15;9(10):1000. doi: 10.3390/antiox9101000. PMID: 33076507; PMCID: PMC7602655. 2. Vijayakumar K, Manigandan V, Jeyapragash D, Bharathidasan V, Anandharaj B, Sathya M. Eucalyptol inhibits biofilm formation of Streptococcus pyogenes and its mediated virulence factors. J Med Microbiol. 2020 Nov;69(11):1308-1318. doi: 10.1099/jmm.0.001253. PMID: 32930658. 3. Mahdavifard S, Nakhjavani M. Preventive Effect of Eucalyptol on the Formation of Aorta Lesions in the Diabetic-Atherosclerotic Rat. Int J Prev Med. 2021 May 26;12:45. doi: 10.4103/ijpvm.IJPVM_319_19. PMID: 34211676; PMCID: PMC8223915. 4. Xu G, Guo J, Sun C. Eucalyptol ameliorates early brain injury after subarachnoid haemorrhage via antioxidant and anti-inflammatory effects in a rat model. Pharm Biol. 2021 Dec;59(1):114-120. doi: 10.1080/13880209.2021.1876101. PMID: 33550883.

In vitro protocol:

In vivo protocol:

1. Mahdavifard S, Nakhjavani M. Preventive Effect of Eucalyptol on the Formation of Aorta Lesions in the Diabetic-Atherosclerotic Rat. Int J Prev Med. 2021 May 26;12:45. doi: 10.4103/ijpvm.IJPVM_319_19. PMID: 34211676; PMCID: PMC8223915. 2. Xu G, Guo J, Sun C. Eucalyptol ameliorates early brain injury after subarachnoid haemorrhage via antioxidant and anti-inflammatory effects in a rat model. Pharm Biol. 2021 Dec;59(1):114-120. doi: 10.1080/13880209.2021.1876101. PMID: 33550883.

1: Frasnelli J, Gingras-Lessard F, Robert J, Steffener J. The Effect of Stimulus Duration on the Nostril Localization of Eucalyptol. Chem Senses. 2017 May 1;42(4):303-308. doi: 10.1093/chemse/bjx008. PubMed PMID: 28334125. 2: Caceres AI, Liu B, Jabba SV, Achanta S, Morris JB, Jordt SE. Transient Receptor Potential Cation Channel Subfamily M Member 8 channels mediate the anti-inflammatory effects of eucalyptol. Br J Pharmacol. 2017 May;174(9):867-879. doi: 10.1111/bph.13760. Epub 2017 Mar 23. PubMed PMID: 28240768; PubMed Central PMCID: PMC5387001. 3: Melo Júnior JM, Damasceno MB, Santos SA, Barbosa TM, Araújo JR, Vieira-Neto AE, Wong DV, Lima-Júnior RC, Campos AR. Acute and neuropathic orofacial antinociceptive effect of eucalyptol. Inflammopharmacology. 2017 Apr;25(2):247-254. doi: 10.1007/s10787-017-0324-5. Epub 2017 Feb 16. PubMed PMID: 28210904. 4: Kendra PE, Montgomery WS, Schnell EQ, Deyrup MA, Epsky ND. Efficacy of α-Copaene, Cubeb, and Eucalyptol Lures for Detection of Redbay Ambrosia Beetle (Coleoptera: Curculionidae: Scolytinae). J Econ Entomol. 2016 Dec;109(6):2428-2435. Epub 2016 Oct 23. PubMed PMID: 27986939. 5: Caldas GF, Limeira MM, Araújo AV, Albuquerque GS, Silva-Neto JD, Silva TG, Costa-Silva JH, Menezes IR, Costa JG, Wanderley AG. Repeated-doses and reproductive toxicity studies of the monoterpene 1,8-cineole (eucalyptol) in Wistar rats. Food Chem Toxicol. 2016 Nov;97:297-306. doi: 10.1016/j.fct.2016.09.020. Epub 2016 Sep 16. PubMed PMID: 27644596. 6: Seol GH, Kim KY. Eucalyptol and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:389-398. PubMed PMID: 27771935. 7: Kennedy-Feitosa E, Okuro RT, Pinho Ribeiro V, Lanzetti M, Barroso MV, Zin WA, Porto LC, Brito-Gitirana L, Valenca SS. Eucalyptol attenuates cigarette smoke-induced acute lung inflammation and oxidative stress in the mouse. Pulm Pharmacol Ther. 2016 Dec;41:11-18. doi: 10.1016/j.pupt.2016.09.004. Epub 2016 Sep 4. PubMed PMID: 27599597. 8: Hąc-Wydro K, Szydło K. The influence of environmentally friendly pesticide - Eucalyptol - alone and in combination with terpinen-4-ol - on model bacterial membranes. Colloids Surf B Biointerfaces. 2016 Oct 1;146:918-23. doi: 10.1016/j.colsurfb.2016.07.044. Epub 2016 Jul 20. PubMed PMID: 27472454. 9: Liu Z, Pan J, Sun C, Zhou J, Li NA. Clinical effects of perazine ferulate tablets combined with eucalyptol limonene pinene enteric soft capsules for treatment of children with IgA nephropathy. Exp Ther Med. 2016 Jul;12(1):169-172. Epub 2016 May 9. PubMed PMID: 27347034; PubMed Central PMCID: PMC4907125. 10: Amnuaikit T, Songkram C, Pinsuwan S. Enhancement of Mycophenolate Mofetil Permeation for Topical Use by Eucalyptol and N-Methyl-2-pyrrolidone. Scientifica (Cairo). 2016;2016:9672718. doi: 10.1155/2016/9672718. Epub 2016 Mar 16. PubMed PMID: 27069715; PubMed Central PMCID: PMC4812526. 11: Alam P, Alqasoumi SI, Abdel-Kader MS. Simultaneous Determination of Menthol and Eucalyptol by the Densitometric HPTLC Method in Some External Analgesic Formulations. J Chromatogr Sci. 2016 Jan;54(1):58-63. doi: 10.1093/chromsci/bmv075. PubMed PMID: 26673189. 12: Jarvis GE, Barbosa R, Thompson AJ. Noncompetitive Inhibition of 5-HT3 Receptors by Citral, Linalool, and Eucalyptol Revealed by Nonlinear Mixed-Effects Modeling. J Pharmacol Exp Ther. 2016 Mar;356(3):549-62. doi: 10.1124/jpet.115.230011. Epub 2015 Dec 15. PubMed PMID: 26669427; PubMed Central PMCID: PMC5378937. 13: Nikolić B, Vasilijević B, Mitić-Ćulafić D, Vuković-Gačić B, Knežević-Vukćević J. Comparative study of genotoxic, antigenotoxic and cytotoxic activities of monoterpenes camphor, eucalyptol and thujone in bacteria and mammalian cells. Chem Biol Interact. 2015 Dec 5;242:263-71. doi: 10.1016/j.cbi.2015.10.012. Epub 2015 Oct 19. PubMed PMID: 26482939. 14: Karataş E, Kol E, Bayrakdar İŞ, Arslan H. The effect of chloroform, orange oil and eucalyptol on root canal transportation in endodontic retreatment. Aust Endod J. 2016 Apr;42(1):37-40. doi: 10.1111/aej.12126. Epub 2015 Sep 29. PubMed PMID: 26420757. 15: Rocha Caldas GF, Oliveira AR, Araújo AV, Lafayette SS, Albuquerque GS, Silva-Neto Jda C, Costa-Silva JH, Ferreira F, Costa JG, Wanderley AG. Gastroprotective Mechanisms of the Monoterpene 1,8-Cineole (Eucalyptol). PLoS One. 2015 Aug 5;10(8):e0134558. doi: 10.1371/journal.pone.0134558. eCollection 2015. PubMed PMID: 26244547; PubMed Central PMCID: PMC4526535. 16: Zeraatpisheh Z, Vatanparast J. Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels. Eur J Pharmacol. 2015 Oct 5;764:70-8. doi: 10.1016/j.ejphar.2015.06.050. Epub 2015 Jun 30. PubMed PMID: 26134504. 17: Khedmat S, Hashemi A, Dibaji F, Kharrazifard MJ. Effect of chloroform, eucalyptol and orange oil solvents on the microhardness of human root dentin. J Dent (Tehran). 2015 Jan;12(1):25-30. PubMed PMID: 26005451; PubMed Central PMCID: PMC4436324. 18: Kim KY, Lee HS, Seol GH. Eucalyptol suppresses matrix metalloproteinase-9 expression through an extracellular signal-regulated kinase-dependent nuclear factor-kappa B pathway to exert anti-inflammatory effects in an acute lung inflammation model. J Pharm Pharmacol. 2015 Aug;67(8):1066-74. doi: 10.1111/jphp.12407. Epub 2015 Mar 13. PubMed PMID: 25773735. 19: Zant D, Gubler DA. The presence of eucalyptol in Artemisia australis validates its use in traditional Hawaiian medicine. Asian Pac J Trop Biomed. 2014 Jul;4(7):520-2. doi: 10.12980/APJTB.4.2014C1112. PubMed PMID: 25183270; PubMed Central PMCID: PMC4032824. 20: Horvathova E, Navarova J, Galova E, Sevcovicova A, Chodakova L, Snahnicanova Z, Melusova M, Kozics K, Slamenova D. Assessment of antioxidative, chelating, and DNA-protective effects of selected essential oil components (eugenol, carvacrol, thymol, borneol, eucalyptol) of plants and intact Rosmarinus officinalis oil. J Agric Food Chem. 2014 Jul 16;62(28):6632-9. doi: 10.1021/jf501006y. Epub 2014 Jul 2. PubMed PMID: 24955655.