Turmerone, ar-(+/-)- | CAS#38142-58-4 | Anti-inflammatory agent

MedKoo Cat#: 462670 | Name: Turmerone, ar-(+/-)-

Description:

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

(+)-ar-Turmerone is an aromatic compound from the rhizomes of C. longa, a perennial plant of the ginger family, Zingiberaceae, commonly used in traditional Asian medicines. It is also a major constituent of essential oil of turmeric, which is known for its antioxidant, anti-inflammatory, and anti-nociceptive properties. Two structurally and physiologically distinct forms of turmerone have been isolated from C. longa, (+)-ar-Turmerone and α-turmerone.1 (+)-ar-Turmerone stimulates the proliferation of peripheral blood mononuclear cells and increases the production of TNF-α, IL-2, and IFN-γ. It also promotes the maturation of dendritic cells and induces the proliferation of neural stem cells both in vitro and in vivo.

Chemical Structure

Turmerone, ar-(+/-)-

CAS#38142-58-4

Theoretical Analysis

MedKoo Cat#: 462670

Name: Turmerone, ar-(+/-)-

CAS#: 38142-58-4

Chemical Formula: C15H20O

Exact Mass: 216.1514

Molecular Weight: 216.32

Elemental Analysis: C, 83.28; H, 9.32; O, 7.40

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Related CAS #

532-65-0 (S-isomer) 38142-58-4

Synonym

(+/-)-ar-Turmerone;

IUPAC/Chemical Name

2-methyl-6-(p-tolyl)hept-2-en-4-one

InChi Key

NAAJVHHFAXWBOK-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H20O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-9,13H,10H2,1-4H3

SMILES Code

CC(c1ccc(C)cc1)CC(/C=C(C)\C)=O

Appearance

Solid powder

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

>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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 216.32 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

1: Chen M, Chang YY, Huang S, Xiao LH, Zhou W, Zhang LY, Li C, Zhou RP, Tang J, Lin L, Du ZY, Zhang K. Aromatic-Turmerone Attenuates LPS-Induced Neuroinflammation and Consequent Memory Impairment by Targeting TLR4-Dependent Signaling Pathway. Mol Nutr Food Res. 2018 Jan;62(2). doi: 10.1002/mnfr.201700281. Epub 2018 Jan 8. PMID: 28849618. 2: Li YL, Du ZY, Li PH, Yan L, Zhou W, Tang YD, Liu GR, Fang YX, Zhang K, Dong CZ, Chen HX. Aromatic-turmerone ameliorates imiquimod-induced psoriasis-like inflammation of BALB/c mice. Int Immunopharmacol. 2018 Nov;64:319-325. doi: 10.1016/j.intimp.2018.09.015. Epub 2018 Sep 19. PMID: 30243067. 3: Hucklenbroich J, Klein R, Neumaier B, Graf R, Fink GR, Schroeter M, Rueger MA. Aromatic-turmerone induces neural stem cell proliferation in vitro and in vivo. Stem Cell Res Ther. 2014 Sep 26;5(4):100. doi: 10.1186/scrt500. PMID: 25928248; PMCID: PMC4180255. 4: Park SY, Jin ML, Kim YH, Kim Y, Lee SJ. Aromatic-turmerone inhibits α-MSH and IBMX-induced melanogenesis by inactivating CREB and MITF signaling pathways. Arch Dermatol Res. 2011 Dec;303(10):737-44. doi: 10.1007/s00403-011-1155-7. Epub 2011 Jun 10. PMID: 21660443. 5: Park SY, Kim YH, Kim Y, Lee SJ. Aromatic-turmerone's anti-inflammatory effects in microglial cells are mediated by protein kinase A and heme oxygenase-1 signaling. Neurochem Int. 2012 Oct;61(5):767-77. doi: 10.1016/j.neuint.2012.06.020. Epub 2012 Jul 3. PMID: 22766494. 6: Liao JC, Tsai JC, Liu CY, Huang HC, Wu LY, Peng WH. Antidepressant-like activity of turmerone in behavioral despair tests in mice. BMC Complement Altern Med. 2013 Nov 1;13:299. doi: 10.1186/1472-6882-13-299. PMID: 24176021; PMCID: PMC3840684. 7: Park SY, Kim YH, Kim Y, Lee SJ. Aromatic-turmerone attenuates invasion and expression of MMP-9 and COX-2 through inhibition of NF-κB activation in TPA- induced breast cancer cells. J Cell Biochem. 2012 Dec;113(12):3653-62. doi: 10.1002/jcb.24238. PMID: 22740037. 8: Kim D, Suh Y, Lee H, Lee Y. Immune activation and antitumor response of ar- turmerone on P388D1 lymphoblast cell implanted tumors. Int J Mol Med. 2013 Feb;31(2):386-92. doi: 10.3892/ijmm.2012.1196. Epub 2012 Nov 29. PMID: 23229920. 9: Yang S, Liu J, Jiao J, Jiao L. Ar-Turmerone Exerts Anti-proliferative and Anti-inflammatory Activities in HaCaT Keratinocytes by Inactivating Hedgehog Pathway. Inflammation. 2020 Apr;43(2):478-486. doi: 10.1007/s10753-019-01131-w. PMID: 31773440. 10: Ji M, Choi J, Lee J, Lee Y. Induction of apoptosis by ar-turmerone on various cell lines. Int J Mol Med. 2004 Aug;14(2):253-6. PMID: 15254774. 11: Orellana-Paucar AM, Afrikanova T, Thomas J, Aibuldinov YK, Dehaen W, de Witte PA, Esguerra CV. Insights from zebrafish and mouse models on the activity and safety of ar-turmerone as a potential drug candidate for the treatment of epilepsy. PLoS One. 2013 Dec 13;8(12):e81634. doi: 10.1371/journal.pone.0081634. PMID: 24349101; PMCID: PMC3862488. 12: Park SY, Jin ML, Kim YH, Kim Y, Lee SJ. Anti-inflammatory effects of aromatic-turmerone through blocking of NF-κB, JNK, and p38 MAPK signaling pathways in amyloid β-stimulated microglia. Int Immunopharmacol. 2012 Sep;14(1):13-20. doi: 10.1016/j.intimp.2012.06.003. Epub 2012 Jun 20. PMID: 22728094. 13: Cheng SB, Wu LC, Hsieh YC, Wu CH, Chan YJ, Chang LH, Chang CM, Hsu SL, Teng CL, Wu CC. Supercritical carbon dioxide extraction of aromatic turmerone from Curcuma longa Linn. induces apoptosis through reactive oxygen species-triggered intrinsic and extrinsic pathways in human hepatocellular carcinoma HepG2 cells. J Agric Food Chem. 2012 Sep 26;60(38):9620-30. doi: 10.1021/jf301882b. Epub 2012 Sep 12. PMID: 22946656. 14: Ali A, Wang YH, Khan IA. Larvicidal and Biting Deterrent Activity of Essential Oils of Curcuma longa, Ar-turmerone, and Curcuminoids Against Aedes aegypti and Anopheles quadrimaculatus (Culicidae: Diptera). J Med Entomol. 2015 Sep;52(5):979-86. doi: 10.1093/jme/tjv072. Epub 2015 Jun 23. PMID: 26336212. 15: Aratanechemuge Y, Komiya T, Moteki H, Katsuzaki H, Imai K, Hibasami H. Selective induction of apoptosis by ar-turmerone isolated from turmeric (Curcuma longa L) in two human leukemia cell lines, but not in human stomach cancer cell line. Int J Mol Med. 2002 May;9(5):481-4. PMID: 11956652. 16: Lee HS. Antiplatelet property of Curcuma longa L. rhizome-derived ar- turmerone. Bioresour Technol. 2006 Aug;97(12):1372-6. doi: 10.1016/j.biortech.2005.07.006. Epub 2005 Aug 19. PMID: 16112857. 17: Lin B, Zhou G, Gong Y, Wei QD, Tian MY, Liu XL, Feng TT, Zhou Y, Yuan WC. Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3'-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Molecules. 2017 Apr 17;22(4):645. doi: 10.3390/molecules22040645. PMID: 28420177; PMCID: PMC6154684. 18: Jankasem M, Wuthi-Udomlert M, Gritsanapan W. Antidermatophytic Properties of Ar-Turmerone, Turmeric Oil, and Curcuma longa Preparations. ISRN Dermatol. 2013 Aug 26;2013:250597. doi: 10.1155/2013/250597. PMID: 24066236; PMCID: PMC3770062. 19: Amaral AC, Gomes LA, Silva JR, Ferreira JL, Ramos Ade S, Rosa Mdo S, Vermelho AB, Rodrigues IA. Liposomal formulation of turmerone-rich hexane fractions from Curcuma longa enhances their antileishmanial activity. Biomed Res Int. 2014;2014:694934. doi: 10.1155/2014/694934. Epub 2014 Jun 18. PMID: 25045693; PMCID: PMC4087288. 20: Aggarwal BB, Yuan W, Li S, Gupta SC. Curcumin-free turmeric exhibits anti- inflammatory and anticancer activities: Identification of novel components of turmeric. Mol Nutr Food Res. 2013 Sep;57(9):1529-42. doi: 10.1002/mnfr.201200838. Epub 2013 Jul 12. PMID: 23847105.