Bisacurone | CAS#120681-81-4 | terpenoid

MedKoo Cat#: 145389 | Name: Bisacurone

Description:

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

Bisacurone is a bioactive terpenoid found in small amounts in turmeric that possesses anti-inflammatory and antioxidant properties. Bisacurone reduces hyperglycemia, protects against body weight (BW) loss, lowers renal markers, reduces lipid profile alterations and avoids histological abnormalities. Bisacurone reduces DN by reducing hyperglycemia, oxidative stress, inflammation, and apoptosis, while also increasing Nrf2/HO-1 signaling.

Chemical Structure

Bisacurone

CAS#120681-81-4

Theoretical Analysis

MedKoo Cat#: 145389

Name: Bisacurone

CAS#: 120681-81-4

Chemical Formula: C15H24O3

Exact Mass: 252.1725

Molecular Weight: 252.35

Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Bisacurone;

IUPAC/Chemical Name

(S)-6-((1R,4S,5S)-4,5-dihydroxy-4-methylcyclohex-2-en-1-yl)-2-methylhept-2-en-4-one

InChi Key

QJOWFYQIUZMPRY-NEBZKDRISA-N

InChi Code

1S/C15H24O3/c1-10(2)7-13(16)8-11(3)12-5-6-15(4,18)14(17)9-12/h5-7,11-12,14,17-18H,8-9H2,1-4H3/t11-,12+,14-,15-/m0/s1

SMILES Code

[H][C@@]1(C[C@H](O)[C@@](C)(O)C=C1)[C@@H](C)CC(=O)C=C(C)C

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 252.35 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: Yang F, Zhang Z, Zhang L. Bisacurone attenuates diabetic nephropathy by ameliorating oxidative stress, inflammation and apoptosis in rats. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221143713. doi: 10.1177/09603271221143713. PMID: 36510688. 2: Ashida H, Tian X, Kitakaze T, Yamashita Y. Bisacurone suppresses hepatic lipid accumulation through inhibiting lipogenesis and promoting lipolysis. J Clin Biochem Nutr. 2020 Jul;67(1):43-52. doi: 10.3164/jcbn.20-16. Epub 2020 May 8. PMID: 32801468; PMCID: PMC7417797. 3: Yan Z, Li S, Gong Z. Bisacurone gel ameliorated burn wounds in experimental rats via its anti-inflammatory, antioxidant, and angiogenic properties. Acta Cir Bras. 2023 Aug 21;38:e382423. doi: 10.1590/acb382423. PMID: 37610964; PMCID: PMC10443232. 4: Miyazawa T, Higuchi O, Sasaki M, Nguyen Thi MT, Miyazawa T. Quantification of Bisacurone and Curcuminoids in Turmeric Products by Liquid Chromatography Coupled with Tandem Mass Spectrometry. J Nutr Sci Vitaminol (Tokyo). 2022;68(2):137-139. doi: 10.3177/jnsv.68.137. PMID: 35491204. 5: He C, Miyazawa T, Abe C, Ueno T, Suzuki M, Mizukami M, Kurihara K, Toda M. Hypolipidemic and Anti-Inflammatory Effects of Curcuma longa-Derived Bisacurone in High-Fat Diet-Fed Mice. Int J Mol Sci. 2023 May 27;24(11):9366. doi: 10.3390/ijms24119366. PMID: 37298318; PMCID: PMC10253162. 6: Koyama K, Hiroshi Sasako, Higashi Y, Ichikawa H, Nagoya A, Hirao T. [Quantitative Analysis of Bisacurone in Turmeric by HPLC Using Relative Molar Sensitivity]. Shokuhin Eiseigaku Zasshi. 2022;63(6):202-209. Japanese. doi: 10.3358/shokueishi.63.202. PMID: 36575034. 7: Sun DI, Nizamutdinova IT, Kim YM, Cai XF, Lee JJ, Kang SS, Kim YS, Kang KM, Chai GY, Chang KC, Kim HJ. Bisacurone inhibits adhesion of inflammatory monocytes or cancer cells to endothelial cells through down-regulation of VCAM-1 expression. Int Immunopharmacol. 2008 Sep;8(9):1272-81. doi: 10.1016/j.intimp.2008.05.006. Epub 2008 Jun 9. PMID: 18602074. 8: Feng LP, Lu LH, Yuan MR, Mei SX, Li XH. Two pairs of bisabolane sesquiterpenoid stereoisomers, bisacurone D-G, from the rhizome of Curcuma longa L. Fitoterapia. 2020 Oct;146:104701. doi: 10.1016/j.fitote.2020.104701. Epub 2020 Aug 4. PMID: 32763365. 9: Nair A, Amalraj A, Jacob J, Kunnumakkara AB, Gopi S. Non-Curcuminoids from Turmeric and Their Potential in Cancer Therapy and Anticancer Drug Delivery Formulations. Biomolecules. 2019 Jan 2;9(1):13. doi: 10.3390/biom9010013. PMID: 30609771; PMCID: PMC6358877. 10: Wang Y, Wang L, Zhu X, Wang D, Li X. Choleretic Activity of Turmeric and its Active Ingredients. J Food Sci. 2016 Jul;81(7):H1800-6. doi: 10.1111/1750-3841.13348. Epub 2016 May 26. PMID: 27228476. 11: 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. 12: An S, Jang E, Lee JH. Preclinical Evidence of Curcuma longa and Its Noncurcuminoid Constituents against Hepatobiliary Diseases: A Review. Evid Based Complement Alternat Med. 2020 Jul 28;2020:8761435. doi: 10.1155/2020/8761435. PMID: 32802138; PMCID: PMC7411463. 13: Uchio R, Higashi Y, Kohama Y, Kawasaki K, Hirao T, Muroyama K, Murosaki S. A hot water extract of turmeric (Curcuma longa) suppresses acute ethanol- induced liver injury in mice by inhibiting hepatic oxidative stress and inflammatory cytokine production. J Nutr Sci. 2017 Jan 12;6:e3. doi: 10.1017/jns.2016.43. PMID: 28620478; PMCID: PMC5465857. 14: Wang LY, Zhang M, Zhang CF, Wang ZT. Alkaloid and sesquiterpenes from the root tuber of Curcuma longa. Yao Xue Xue Bao. 2008 Jul;43(7):724-7. PMID: 18819476. 15: Kawasaki K, Muroyama K, Murosaki S. Effect of a water extract of Curcuma longa on emotional states in healthy participants. Biosci Microbiota Food Health. 2018;37(2):25-29. doi: 10.12938/bmfh.17-020. Epub 2018 Feb 2. PMID: 29662734; PMCID: PMC5897237. 16: Liao Y, Zhang X, Cao D, Wang F, Chen H, Li R. Separation and identification of terpene-conjugated curcuminoids based on liquid chromatography-tandem mass spectrometry and their in vitro anti-inflammatory activities. J Sep Sci. 2023 May;46(10):e2200789. doi: 10.1002/jssc.202200789. Epub 2023 Mar 17. PMID: 36892097. 17: Uchio R, Okuda-Hanafusa C, Sakaguchi H, Saji R, Muroyama K, Murosaki S, Yamamoto Y, Hirose Y. Curcuma longa extract reduces serum inflammatory markers and postprandial hyperglycemia in healthy but borderline participants with overweight and glycemia in the normal/prediabetes range: a randomized, double-blind, and placebo-controlled trial. Front Nutr. 2024 Jan 29;11:1324196. doi: 10.3389/fnut.2024.1324196. PMID: 38347961; PMCID: PMC10859506. 18: Uchio R, Muroyama K, Okuda-Hanafusa C, Kawasaki K, Yamamoto Y, Murosaki S. Hot Water Extract of Curcuma longa L. Improves Serum Inflammatory Markers and General Health in Subjects with Overweight or Prehypertension/Mild Hypertension: A Randomized, Double-Blind, Placebo-Controlled Trial. Nutrients. 2019 Aug 7;11(8):1822. doi: 10.3390/nu11081822. PMID: 31394768; PMCID: PMC6723939. 19: Li W, Feng JT, Xiao YS, Wang YQ, Xue XY, Liang XM. Three novel terpenoids from the rhizomes of Curcuma longa. J Asian Nat Prod Res. 2009 Jun;11(6):569-75. doi: 10.1080/10286020902939182. PMID: 20183292. 20: Amalraj A, Jude S, Varma K, Jacob J, Gopi S, Oluwafemi OS, Thomas S. Preparation of a novel bioavailable curcuminoid formulation (Cureit™) using Polar-Nonpolar-Sandwich (PNS) technology and its characterization and applications. Mater Sci Eng C Mater Biol Appl. 2017 Jun 1;75:359-367. doi: 10.1016/j.msec.2017.02.068. Epub 2017 Feb 15. PMID: 28415473.