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MedKoo Cat#: 145291 | Name: Shyobunone

Description:

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

Shyobunone is a compound of Siparuna guianensis essential oil. Shyobunone and its derivatives strongly interact with AChE with a kind of non-competitive inhibition. Shyobunone has a GABAA positive modulating effect.

Chemical Structure

Shyobunone
Shyobunone
CAS#21698-44-2

Theoretical Analysis

MedKoo Cat#: 145291

Name: Shyobunone

CAS#: 21698-44-2

Chemical Formula: C15H24O

Exact Mass: 220.1827

Molecular Weight: 220.36

Elemental Analysis: C, 81.76; H, 10.98; O, 7.26

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.
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Related CAS #
No Data
Synonym
Shyobunone; Shyobunon;
IUPAC/Chemical Name
(2S,3S,6S)-6-isopropyl-3-methyl-2-(prop-1-en-2-yl)-3-vinylcyclohexan-1-one
InChi Key
GWHRSRIPLDHJHR-GZBFAFLISA-N
InChi Code
1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12-13H,1,4,8-9H2,2-3,5-6H3/t12-,13+,15+/m0/s1
SMILES Code
CC(C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 220.36 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: Chen HP, Yang K, Zheng LS, You CX, Cai Q, Wang CF. Repellant and insecticidal activities of shyobunone and isoshyobunone derived from the essential oil of Acorus calamus rhizomes. Pharmacogn Mag. 2015 Oct-Dec;11(44):675-81. doi: 10.4103/0973-1296.165543. PMID: 26600710; PMCID: PMC4621634. 2: Martins RMG, Xavier-Júnior FH, Barros MR, Menezes TM, de Assis CRD, de Melo ACGR, Veras BO, Ferraz VP, Filho AAM, Yogui GT, Bezerra RS, Seabra GM, Neves JL, Tadei WP. Impact on cholinesterase-inhibition and in silico investigations of sesquiterpenoids from Amazonian Siparuna guianensis Aubl. Spectrochim Acta A Mol Biomol Spectrosc. 2021 May 5;252:119511. doi: 10.1016/j.saa.2021.119511. Epub 2021 Jan 29. PMID: 33561686. 3: Lalia A, Harizia A, Righi K, Daikh ZE. Chemical composition and allelopathic potential of Schinus molle L. (Anacardiaceae) essential oils against common weeds of wheat crop. Nat Prod Res. 2023 Nov 25:1-7. doi: 10.1080/14786419.2023.2287174. Epub ahead of print. PMID: 38006326. 4: Parki A, Chaubey P, Prakash O, Kumar R, Pant AK. Seasonal Variation in Essential Oil Compositions and Antioxidant Properties of Acorus calamus L. Accessions. Medicines (Basel). 2017 Nov 8;4(4):81. doi: 10.3390/medicines4040081. PMID: 29117116; PMCID: PMC5750605. 5: Xin Z, Ren D, Zhang X, Yi Z, Yi L. Chromatographic Fingerprints Combined with Chemometric Methods Reveal the Chemical Features of Authentic Radix Polygalae. J AOAC Int. 2017 Jan 1;100(1):30-37. doi: 10.5740/jaoacint.16-0225. Epub 2016 Oct 13. PMID: 27743444. 6: Zaugg J, Eickmeier E, Ebrahimi SN, Baburin I, Hering S, Hamburger M. Positive GABA(A) receptor modulators from Acorus calamus and structural analysis of (+)-dioxosarcoguaiacol by 1D and 2D NMR and molecular modeling. J Nat Prod. 2011 Jun 24;74(6):1437-43. doi: 10.1021/np200181d. Epub 2011 May 12. PMID: 21563811; PMCID: PMC3199944. 7: Tosun F, Göger F, İşcan G, Kürkçüoğlu M, Kuran FK, Miski M. Biological Activities of the Fruit Essential Oil, Fruit, and Root Extracts of Ferula drudeana Korovin, the Putative Anatolian Ecotype of the Silphion Plant. Plants (Basel). 2023 Feb 13;12(4):830. doi: 10.3390/plants12040830. PMID: 36840178; PMCID: PMC9959981. 8: Bertea CM, Azzolin CM, Bossi S, Doglia G, Maffei ME. Identification of an EcoRI restriction site for a rapid and precise determination of beta-asarone- free Acorus calamus cytotypes. Phytochemistry. 2005 Mar;66(5):507-14. doi: 10.1016/j.phytochem.2005.01.007. PMID: 15721942. 9: Huang X, Li GC, Yin L, Zhang ZH, Liang YX, Chen HB. [The effective parts of liangxue tongyu prescription on cooling-blood and activating-blood and analysis of chemical constituents by HPLC-MS and GC-MS]. Yao Xue Xue Bao. 2015 Jan;50(1):86-93. Chinese. PMID: 25924481. 10: St-Gelais A, Mathieu M, Levasseur V, Ovando JF, Escamilla R, Marceau H. Preisocalamendiol, Shyobunol and Related Oxygenated Sesquiterpenes from Bolivian Schinus molle Essential Oil. Nat Prod Commun. 2016 Apr;11(4):547-50. PMID: 27396215. 11: Khan M, Mousa AA, Syamasundar KV, Alkhathlan HZ. Determination of chemical constituents of leaf and stem essential oils of Artemisia monosperma from central Saudi Arabia. Nat Prod Commun. 2012 Aug;7(8):1079-82. PMID: 22978234. 12: Liu Z, Zheng Z, Wang T, Liu Z, Zuo Z. Using ultra-performance liquid chromatography with linear ion trap-electrostatic field orbitrap mass spectrometry, network pharmacology, and molecular docking to explore the constituent targets and action mechanisms of decoction of Angelica sinensis, Zingiberis Rhizoma Recens, and Mutton in the treatment of diarrhea-predominant irritable bowel syndrome. J Pharm Pharmacol. 2024 May 3;76(5):462-478. doi: 10.1093/jpp/rgad076. PMID: 37832514. 13: Stahl E, Keller K. Extraktion labiler Naturstoffe mit überkritischen Gasen [Extraction of thermolabile compounds with supercritical gases.]. Planta Med. 1983 Feb;47(2):75-8. German. doi: 10.1055/s-2007-969955. PMID: 17405097.