Myrtenal | CAS#564-94-3 | Inhibitor of Acetylcholinesterase, Antioxidant Stabilizer

MedKoo Cat#: 584155 | Name: Myrtenal

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Description:

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

Myrtenal is a natural monoterpene that occurs in plants such as cumin, pepper, mint and eucalyptus. It was found to attenuate diethylnitrosamine-induced hepatocellular carcinoma in rats by stabilizing intrinsic antioxidants and modulating apoptotic and anti-apoptotic cascades. Myrtenal has also shown activity as an inhibiting agent of acetylcholinesterase, a known Alzheimer target.

Chemical Structure

Myrtenal

CAS#564-94-3

Theoretical Analysis

MedKoo Cat#: 584155

Name: Myrtenal

CAS#: 564-94-3

Chemical Formula: C10H14O

Exact Mass: 150.1045

Molecular Weight: 150.22

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

Price and Availability

Size	Price	Availability
10g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks
100g	USD 950.00	2 Weeks
200g	USD 1,450.00	2 Weeks
500g	USD 2,450.00	2 Weeks
1kg	USD 3,650.00	2 Weeks

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Related CAS #

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Synonym

Myrtenal; Benihinal; NSC 54384; NSC-54384; NSC54384

IUPAC/Chemical Name

2-Norpinene-2-carboxaldehyde, 6,6-dimethyl- (8CI)

InChi Key

KMRMUZKLFIEVAO-UHFFFAOYSA-N

InChi Code

InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3

SMILES Code

O=CC1=CCC2CC1C2(C)C

Appearance

Clear liquid

Purity

>97% (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

Certificate of Analysis

View CoA: current batch, Lot#S9G04M23

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Myrtenal is a natural monoterpene that occurs in plants such as cumin, pepper, mint and eucalyptus.

In vitro activity:

The inhibition of V-ATPases by 100 μM Myrtenal disrupted the electrochemical H+ gradient across the cell membranes, strongly induced cell death (4-5 fold), and decreased tumor cells migration and invasion in vitro. These data revealed the therapeutic potential of Myrtenal as inhibitor of melanoma progression proposing a mechanism of action by which once inhibited by this monoterpene the proton pumps fail to activate cancer-related differential electrochemical gradients and H+ fluxes across the tumor cell membranes, disrupting pH signatures inherent in tumor progression, resulting in reprogrammed cell death and metastasis inhibition. Reference: Biochim Biophys Acta Gen Subj. 2019 Jan;1863(1):1-12. https://pubmed.ncbi.nlm.nih.gov/30279148/

In vivo activity:

The present study is proposed to determine the anti-atherosclerotic activity of Myrtenal in high-fat diet-induced atherosclerosis (AS) rat models. The Myrtenal-treated groups exhibited a decreased TC, TG, and LDLc levels; increased HDLc levels; and a decline in the inflammatory cytokines such as CRP, IL-1β, IL-8, and IL-18 when compared to the untreated AS rats. Furthermore, Myrtenal decreased ET, TXB2, and 6-keto-PGF1α levels indicating its anti-atherosclerotic activity. Reference: Appl Biochem Biotechnol. 2022 Dec;194(12):5717-5733. https://pubmed.ncbi.nlm.nih.gov/35804285/

Preparing Stock Solutions

The following data is based on the product molecular weight 150.22 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. Martins BX, Arruda RF, Costa GA, Jerdy H, de Souza SB, Santos JM, de Freitas WR, Kanashiro MM, de Carvalho ECQ, Sant'Anna NF, Antunes F, Martinez-Zaguilan R, Souad S, Okorokova-Façanha AL, Façanha AR. Myrtenal-induced V-ATPase inhibition - A toxicity mechanism behind tumor cell death and suppressed migration and invasion in melanoma. Biochim Biophys Acta Gen Subj. 2019 Jan;1863(1):1-12. doi: 10.1016/j.bbagen.2018.09.006. Epub 2018 Sep 11. PMID: 30279148. 2. Hari Babu L, Perumal S, Balasubramanian MP. Myrtenal attenuates diethylnitrosamine-induced hepatocellular carcinoma in rats by stabilizing intrinsic antioxidants and modulating apoptotic and anti-apoptotic cascades. Cell Oncol (Dordr). 2012 Aug;35(4):269-83. doi: 10.1007/s13402-012-0086-4. Epub 2012 Jun 22. PMID: 22722977. 3. Yu L, Liu H, Ma X, Seshadri VD, Gao X. Anti-atherosclerotic Effects of Myrtenal in High-Fat Diet-Induced Atherosclerosis in Rats. Appl Biochem Biotechnol. 2022 Dec;194(12):5717-5733. doi: 10.1007/s12010-022-04044-x. Epub 2022 Jul 9. PMID: 35804285. 4. Akefe IO, Adegoke VA, Lamidi IY, Ameh MP, Idoga ES, Ubah SA, Ajayi IE. Myrtenal mitigates streptozotocin-induced spatial memory deficit via improving oxido inflammatory, cholinergic and neurotransmitter functions in mice. Curr Res Pharmacol Drug Discov. 2022 May 4;3:100106. doi: 10.1016/j.crphar.2022.100106. PMID: 35570857; PMCID: PMC9095925.

In vitro protocol:

In vivo protocol:

1. Yu L, Liu H, Ma X, Seshadri VD, Gao X. Anti-atherosclerotic Effects of Myrtenal in High-Fat Diet-Induced Atherosclerosis in Rats. Appl Biochem Biotechnol. 2022 Dec;194(12):5717-5733. doi: 10.1007/s12010-022-04044-x. Epub 2022 Jul 9. PMID: 35804285. 2. Akefe IO, Adegoke VA, Lamidi IY, Ameh MP, Idoga ES, Ubah SA, Ajayi IE. Myrtenal mitigates streptozotocin-induced spatial memory deficit via improving oxido inflammatory, cholinergic and neurotransmitter functions in mice. Curr Res Pharmacol Drug Discov. 2022 May 4;3:100106. doi: 10.1016/j.crphar.2022.100106. PMID: 35570857; PMCID: PMC9095925.

1: Lin GS, Duan WG, Yang LX, Huang M, Lei FH. Synthesis and Antifungal Activity of Novel Myrtenal-Based 4-Methyl-1,2,4-triazole-thioethers. Molecules. 2017 Jan 24;22(2). pii: E193. doi: 10.3390/molecules22020193. PubMed PMID: 28125042. 2: Rathinam A, Pari L. Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats. Chem Biol Interact. 2016 Aug 25;256:161-6. doi: 10.1016/j.cbi.2016.07.009. Epub 2016 Jul 11. PubMed PMID: 27417257. 3: Clay JM, Hesek D, Oliver AG, Lee M, Fisher JF. Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal. J Org Chem. 2016 Jul 1;81(13):5705-9. doi: 10.1021/acs.joc.6b00756. Epub 2016 Jun 23. PubMed PMID: 27281133. 4: Ayyasamy R, Leelavinothan P. Myrtenal alleviates hyperglycaemia, hyperlipidaemia and improves pancreatic insulin level in STZ-induced diabetic rats. Pharm Biol. 2016 Nov;54(11):2521-2527. Epub 2016 May 9. PubMed PMID: 27158912. 5: Booupathy LK, Venkatachalam S, Natarajan N, Thamaraiselvan R, Arumugam M, Maruthaiveeran Periyasamy B. Chemopreventive effect of myrtenal on bacterial enzyme activity and the development of 1,2-dimethyl hydrazine-induced aberrant crypt foci in Wistar Rats. J Food Drug Anal. 2016 Jan;24(1):206-213. doi: 10.1016/j.jfda.2015.07.003. Epub 2015 Dec 11. PubMed PMID: 28911405. 6: Lokeshkumar B, Sathishkumar V, Nandakumar N, Rengarajan T, Madankumar A, Balasubramanian MP. Anti-Oxidative Effect of Myrtenal in Prevention and Treatment of Colon Cancer Induced by 1, 2-Dimethyl Hydrazine (DMH) in Experimental Animals. Biomol Ther (Seoul). 2015 Sep;23(5):471-8. doi: 10.4062/biomolther.2015.039. Epub 2015 Sep 1. PubMed PMID: 26336588; PubMed Central PMCID: PMC4556208. 7: Rathinam A, Pari L, Chandramohan R, Sheikh BA. Histopathological findings of the pancreas, liver, and carbohydrate metabolizing enzymes in STZ-induced diabetic rats improved by administration of myrtenal. J Physiol Biochem. 2014 Dec;70(4):935-46. doi: 10.1007/s13105-014-0362-z. Epub 2014 Oct 8. PubMed PMID: 25292424. 8: Goretti M, Turchetti B, Cramarossa MR, Forti L, Buzzini P. Production of flavours and fragrances via bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by non-conventional yeast whole-cells. Molecules. 2013 May 16;18(5):5736-48. doi: 10.3390/molecules18055736. PubMed PMID: 23681058. 9: Babu LH, Perumal S, Balasubramanian MP. Myrtenal, a natural monoterpene, down-regulates TNF-α expression and suppresses carcinogen-induced hepatocellular carcinoma in rats. Mol Cell Biochem. 2012 Oct;369(1-2):183-93. doi: 10.1007/s11010-012-1381-0. Epub 2012 Jul 5. PubMed PMID: 22763672. 10: Hari Babu L, Perumal S, Balasubramanian MP. Myrtenal attenuates diethylnitrosamine-induced hepatocellular carcinoma in rats by stabilizing intrinsic antioxidants and modulating apoptotic and anti-apoptotic cascades. Cell Oncol (Dordr). 2012 Aug;35(4):269-83. doi: 10.1007/s13402-012-0086-4. Epub 2012 Jun 22. PubMed PMID: 22722977. 11: Lingaiah HB, Natarajan N, Thamaraiselvan R, Srinivasan P, Periyasamy BM. Myrtenal ameliorates diethylnitrosamine-induced hepatocarcinogenesis through the activation of tumor suppressor protein p53 and regulation of lysosomal and mitochondrial enzymes. Fundam Clin Pharmacol. 2013 Aug;27(4):443-54. doi: 10.1111/j.1472-8206.2012.01039.x. Epub 2012 Mar 21. PubMed PMID: 22436021. 12: Kaufmann D, Dogra AK, Wink M. Myrtenal inhibits acetylcholinesterase, a known Alzheimer target. J Pharm Pharmacol. 2011 Oct;63(10):1368-71. doi: 10.1111/j.2042-7158.2011.01344.x. Epub 2011 Aug 19. PubMed PMID: 21899553. 13: Kawashima H, Goto H. Synthesis and Properties of a Chiroptically Active Oligomer from 3,4-Ethylenedioxythiophene and (-)-Myrtenal. Materials (Basel). 2011 May 30;4(6):1013-1022. doi: 10.3390/ma4061013. PubMed PMID: 28879964; PubMed Central PMCID: PMC5448632. 14: Zepeda LG, Burgueño-Tapia E, Joseph-Nathan P. Myrtenal, a controversial molecule for the proper application of the CIP Sequence Rule for multiple bonds. Nat Prod Commun. 2011 Apr;6(4):429-32. PubMed PMID: 21560753. 15: Burgueño-Tapia E, Zepeda LG, Joseph-Nathan P. Absolute configuration of (-)-myrtenal by vibrational circular dichroism. Phytochemistry. 2010 Jul;71(10):1158-61. doi: 10.1016/j.phytochem.2010.04.005. Epub 2010 May 8. PubMed PMID: 20457457. 16: Otero A, Fernandez-Baeza J, Antiñolo A, Tejeda J, Lara-Sanchez A, Sanchez-Barba LF, Sanchez-Molina M, Franco S, López-Solera MI, Rodríguez AM. Highly diastereoselective nucleophilic addition to myrtenal. Straightforward synthesis of an enantiopure scorpionate ligand. Inorg Chem. 2007 Oct 15;46(21):8475-7. Epub 2007 Sep 21. PubMed PMID: 17883268. 17: Vargas-Díaz ME, Joseph-Nathan P, Tamariz J, Zepeda LG. Synthesis of a new (1R)-(-)-myrtenal-derived dioxadithiadodecacycle and its use as an efficient chiral auxiliary. Org Lett. 2007 Jan 4;9(1):13-6. PubMed PMID: 17192073. 18: Dufrasne F, Gelbcke M, Galanski M. Signal separation and determination of the enantiomeric purity of primary amines with (-)-myrtenal--a 13C NMR study. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Nov;65(3-4):869-73. Epub 2006 May 5. PubMed PMID: 16678477. 19: Solladié-Cavallo A, Balaz M, Salisova M, Welter R. New 1,3-oxathianes derived from myrtenal: synthesis and reactivity. J Org Chem. 2003 Aug 22;68(17):6619-26. PubMed PMID: 12919025. 20: Dufrasne F, Gelbcke M, Nève J. 1H-nuclear magnetic resonance determination of the enantiomeric purity of aliphatic primary amines, beta-aminoalcohols, beta-diamines and alpha-amino-acids with 1R-(-)-myrtenal: scope and limitations. Spectrochim Acta A Mol Biomol Spectrosc. 2003 Apr;59(6):1239-45. PubMed PMID: 12659892.