Germacrone | CAS#6902-91-6 | PPV antiviral

MedKoo Cat#: 561656 | Name: Germacrone

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Description:

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

Germacrone is a natural antiviral agent against porcine parvovirus (PPV).

Chemical Structure

Germacrone

CAS#6902-91-6

Theoretical Analysis

MedKoo Cat#: 561656

Name: Germacrone

CAS#: 6902-91-6

Chemical Formula: C15H22O

Exact Mass: 218.1671

Molecular Weight: 218.34

Elemental Analysis: C, 82.52; H, 10.16; O, 7.33

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Germacrone; Germacron; (E,E)-Germacrone;

IUPAC/Chemical Name

(3E,7E)-3,7-Dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dienone

InChi Key

CAULGCQHVOVVRN-SWZPTJTJSA-N

InChi Code

InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+

SMILES Code

C/C(C)=C1C/C=C(C)/CC/C=C(C)/CC\1=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

>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

Instruction

View handling instruction

Biological target:

Germacrone inhibits influenza virus infection.

In vitro activity:

MTT assay results designated potential inhibition of osteosarcoma cell viability by germacrone drug in a dose and time-reliant manner. Further, phase contrast inverted microscopy depicted significant morphological changes in osteosarcoma cells after germacrone exposure, which were indicative of autophagic cell death. Reference: Acta Biochim Pol. 2022 Apr 25;69(2):305-308. https://pubmed.ncbi.nlm.nih.gov/35468267/

In vivo activity:

The body weight of the mice did not differ between the GM (germacrone)- and the vehicle-treated groups (Fig. 6A). However, administration of GM markedly attenuated the volume and the weight of the tumors in a dose-dependent manner compared with the corresponding parameters in the vehicle group (Fig. 6B-D). Moreover, higher levels of ROS, determined by stronger fluorescence staining with DHE, were also observed in the GM treatment groups (Fig. 6E). In addition, GM administration substantially promoted the formation of cleaved caspase-3 and GSDME-N in a dose-dependent manner (Fig. 6F and G), which was consistent with the results of the in vitro studies on HepG2 cells. Therefore, these results indicated that GM treatment could reduce tumor volume by inducing pyroptosis in a mouse xenograft model. Reference: Exp Ther Med. 2022 May 20;24(1):456. https://pubmed.ncbi.nlm.nih.gov/35747157/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	91.60
	DMF:PBS (pH 7.2) (1:8)	0.1	0.50
	DMSO	51.0	233.58
	Ethanol	15.0	68.70

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 218.34 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. Li E, Gao Y, Mou L, Zhang Z. Anticancer activity of Germacrone terpenoid in human osteosarcoma cells is mediated via autophagy induction, cell cycle disruption, downregulating the cell cycle regulatory protein expressions and cell migration inhibition. Acta Biochim Pol. 2022 Apr 25;69(2):305-308. doi: 10.18388/abp.2020_5712. PMID: 35468267. 2. Lin M, Li P, Liu W, Niu T, Huang L. Germacrone alleviates okadaic acid-induced neurotoxicity in PC12 cells via M1 muscarinic receptor-mediated Galphaq (Gq)/phospholipase C beta (PLCβ)/ protein kinase C (PKC) signaling. Bioengineered. 2022 Mar;13(3):4898-4910. doi: 10.1080/21655979.2022.2036918. PMID: 35156515; PMCID: PMC8974147. 3. Sun X, Zhong X, Ma W, Feng W, Huang Q, Ma M, Lv M, Hu R, Han Z, Li J, Zhou X. Germacrone induces caspase-3/GSDME activation and enhances ROS production, causing HepG2 pyroptosis. Exp Ther Med. 2022 May 20;24(1):456. doi: 10.3892/etm.2022.11383. PMID: 35747157; PMCID: PMC9204551. 4. Zhuang S, Liu B, Guo S, Xue Y, Wu L, Liu S, Zhang C, Ni X. Germacrone alleviates neurological deficits following traumatic brain injury by modulating neuroinflammation and oxidative stress. BMC Complement Med Ther. 2021 Jan 5;21(1):6. doi: 10.1186/s12906-020-03175-0. PMID: 33402180; PMCID: PMC7786997.

In vitro protocol:

In vivo protocol:

1. Sun X, Zhong X, Ma W, Feng W, Huang Q, Ma M, Lv M, Hu R, Han Z, Li J, Zhou X. Germacrone induces caspase-3/GSDME activation and enhances ROS production, causing HepG2 pyroptosis. Exp Ther Med. 2022 May 20;24(1):456. doi: 10.3892/etm.2022.11383. PMID: 35747157; PMCID: PMC9204551. 2. Zhuang S, Liu B, Guo S, Xue Y, Wu L, Liu S, Zhang C, Ni X. Germacrone alleviates neurological deficits following traumatic brain injury by modulating neuroinflammation and oxidative stress. BMC Complement Med Ther. 2021 Jan 5;21(1):6. doi: 10.1186/s12906-020-03175-0. PMID: 33402180; PMCID: PMC7786997.

1: Zárybnický T, Boušová I, Ambrož M, Skálová L. Hepatotoxicity of monoterpenes and sesquiterpenes. Arch Toxicol. 2017 Sep 13. doi: 10.1007/s00204-017-2062-2. [Epub ahead of print] Review. PubMed PMID: 28905185. 2: 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. Review. PubMed PMID: 23847105. 3: Lu JJ, Dang YY, Huang M, Xu WS, Chen XP, Wang YT. Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae--a review. J Ethnopharmacol. 2012 Sep 28;143(2):406-11. doi: 10.1016/j.jep.2012.07.009. Epub 2012 Jul 20. Review. PubMed PMID: 22820242. 4: Ishida T. Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chem Biodivers. 2005 May;2(5):569-90. Review. PubMed PMID: 17192005.