Psilostachyin C | 6466-67-7

MedKoo Cat#: 581713 | Name: Psilostachyin C

Description:

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

Psilostachyin c is a member of the class of compounds known as ambrosanolides and secoambrosanolides. Ambrosanolides and secoambrosanolides are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Psilostachyin c is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Psilostachyin c can be found in mugwort, which makes psilostachyin c a potential biomarker for the consumption of this food product.

Chemical Structure

Psilostachyin C

CAS#6466-67-7

Theoretical Analysis

MedKoo Cat#: 581713

Name: Psilostachyin C

CAS#: 6466-67-7

Chemical Formula: C15H20O4

Exact Mass: 264.1362

Molecular Weight: 264.32

Elemental Analysis: C, 68.16; H, 7.63; O, 24.21

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

Psilostachyin C; NSC 106392.

IUPAC/Chemical Name

(3aR,6R,6aR,10aR,10bS)-6,10a-dimethyl-3-methylenedecahydrofuro[3',2':6,7]cyclohepta[1,2-b]pyran-2,9-dione

InChi Key

FZYIWDQVFMUXPW-UMJOCOHISA-N

InChi Code

InChI=1S/C15H20O4/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(16)19-15/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10-,11-,13+,15-/m1/s1

SMILES Code

O1[C@@H]2[C@@]3(OC(=O)CC[C@@H]3[C@@H](CC[C@@H]2C(=C)C1=O)C)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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 264.32 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: Sülsen VP, Puente V, Papademetrio D, Batlle A, Martino VS, Frank FM, Lombardo ME. Mode of Action of the Sesquiterpene Lactones Psilostachyin and Psilostachyin C on Trypanosoma cruzi. PLoS One. 2016 Mar 3;11(3):e0150526. doi: 10.1371/journal.pone.0150526. eCollection 2016. PubMed PMID: 26939119; PubMed Central PMCID: PMC4777292. 2: Martino R, Beer MF, Elso O, Donadel O, Sülsen V, Anesini C. Sesquiterpene lactones from Ambrosia spp. are active against a murine lymphoma cell line by inducing apoptosis and cell cycle arrest. Toxicol In Vitro. 2015 Oct;29(7):1529-36. doi: 10.1016/j.tiv.2015.06.011. Epub 2015 Jun 15. PubMed PMID: 26086122. 3: Barrera P, Sülsen VP, Lozano E, Rivera M, Beer MF, Tonn C, Martino VS, Sosa MA. Natural Sesquiterpene Lactones Induce Oxidative Stress in Leishmania mexicana. Evid Based Complement Alternat Med. 2013;2013:163404. doi: 10.1155/2013/163404. Epub 2013 Jun 4. PubMed PMID: 23861697; PubMed Central PMCID: PMC3687511. 4: Sülsen VP, Frank FM, Cazorla SI, Barrera P, Freixa B, Vila R, Sosa MA, Malchiodi EL, Muschietti LV, Martino VS. Psilostachyin C: a natural compound with trypanocidal activity. Int J Antimicrob Agents. 2011 Jun;37(6):536-43. doi: 10.1016/j.ijantimicag.2011.02.003. Epub 2011 Apr 15. PubMed PMID: 21497061. 5: Li C, Tu S, Wen S, Li S, Chang J, Shao F, Lei X. Total synthesis of the G2/M DNA damage checkpoint inhibitor psilostachyin C. J Org Chem. 2011 May 6;76(9):3566-70. doi: 10.1021/jo2001275. Epub 2011 Mar 21. PubMed PMID: 21417227. 6: Csupor-Löffler B, Hajdú Z, Zupkó I, Réthy B, Falkay G, Forgo P, Hohmann J. Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines. Phytother Res. 2009 May;23(5):672-6. doi: 10.1002/ptr.2697. PubMed PMID: 19107850. 7: Wang PH, Xu J, Wu MY. [Chemical constituents of ragweed (Ambrosia artemisiifolia L.)]. Zhongguo Zhong Yao Za Zhi. 1993 Mar;18(3):164-6, 191. Chinese. PubMed PMID: 8352903.