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MedKoo Cat#: 573245 | Name: ar-Turmerone
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Description:

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

ar-Turmerone is an immunomodulator which has exhibited cytotoxicity toward various cell lines such as the K562, L1210, U937 and RBL-2H3 cell lines.

Chemical Structure

ar-Turmerone
ar-Turmerone
CAS#532-65-0 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 573245

Name: ar-Turmerone

CAS#: 532-65-0 (S-isomer)

Chemical Formula: C15H20O

Exact Mass: 216.1514

Molecular Weight: 216.32

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

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 Weeks
10mg USD 950.00 2 Weeks
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Related CAS #
532-65-0 (S-isomer) 38142-58-4
Synonym
(+)-ar-Turmerone, ar-(+)-Turmerone, aromatic-turmerone, ar-Turmerone, (S)-ar-Turmerone
IUPAC/Chemical Name
2-Hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (S)-
InChi Key
NAAJVHHFAXWBOK-ZDUSSCGKSA-N
InChi Code
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/t13-/m0/s1
SMILES Code
C\C(=C\C(C[C@H](C)c1ccc(cc1)C)=O)C
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

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.

Recalculate based on batch purity %
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: 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. 2: Li Z, Sun Y, Gu L, Wang Y, Xu M, Zhou Y, Hu Y, Ma W. Ar-turmerone suppresses Aspergillus flavus growth and aflatoxin accumulation: Finding a new antifungal agent based on stored maize. Food Res Int. 2023 Jun;168:112735. doi: 10.1016/j.foodres.2023.112735. Epub 2023 Mar 22. PMID: 37120196. 3: Kongpol K, Sermkaew N, Makkliang F, Khongphan S, Chuaboon L, Sakdamas A, Sakamoto S, Putalun W, Yusakul G. Extraction of curcuminoids and ar-turmerone from turmeric (Curcuma longa L.) using hydrophobic deep eutectic solvents (HDESs) and application as HDES-based microemulsions. Food Chem. 2022 Dec 1;396:133728. doi: 10.1016/j.foodchem.2022.133728. Epub 2022 Jul 16. PMID: 35870240. 4: Liu J, Fernandez D, Gao Y, Pierre S, Gao Y, Dai G. Enzymology, Histological and Ultrastructural Effects of Ar-Turmerone on Culex pipiens pallens Larvae. Insects. 2020 May 30;11(6):336. doi: 10.3390/insects11060336. PMID: 32486189; PMCID: PMC7349101. 5: Rao P, Goswami D, Rawal RM. Molecular insights on ar-turmerone as a structural, functional and pharmacophoric analogue of synthetic mosquito repellent DEET by comprehensive computational assessment. Sci Rep. 2022 Sep 16;12(1):15564. doi: 10.1038/s41598-022-19901-2. PMID: 36114273; PMCID: PMC9481521. 6: Ali AH, Agustar HK, Hassan NI, Latip J, Embi N, Sidek HM. Data on antiplasmodial and stage-specific inhibitory effects of Aromatic (Ar)-Turmerone against Plasmodium falciparum 3D7. Data Brief. 2020 Nov 26;33:106592. doi: 10.1016/j.dib.2020.106592. PMID: 33318979; PMCID: PMC7725727. 7: 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. 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: 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. 10: Li C, Zhang W, Wu X, Cai Q, Tan Z, Hong Z, Huang S, Yuan Y, Yao L, Zhang L. Aromatic-turmerone ameliorates DSS-induced ulcerative colitis via modulating gut microbiota in mice. Inflammopharmacology. 2022 Aug;30(4):1283-1294. doi: 10.1007/s10787-022-01007-w. Epub 2022 Jul 6. PMID: 35794287. 11: Saga Y, Hatakenaka Y, Matsumoto M, Yoshioka Y, Matsumura S, Zaima N, Konishi Y. Neuroprotective effects of aromatic turmerone on activity deprivation-induced apoptosis in cerebellar granule neurons. Neuroreport. 2020 Dec 16;31(18):1302-1307. doi: 10.1097/WNR.0000000000001551. PMID: 33165195. 12: 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. 13: 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. 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: 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. 16: 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. 17: 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. 18: 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. 19: 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. 20: 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.