IUPAC/Chemical Name
(4aR,10aS)-6-hydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid
InChi Key
ATHWSPHADLLZSS-PXNSSMCTSA-N
InChi Code
InChI=1S/C20H28O3/c1-12(2)14-10-13-6-7-17-19(3,4)8-5-9-20(17,18(22)23)15(13)11-16(14)21/h10-12,17,21H,5-9H2,1-4H3,(H,22,23)/t17-,20-/m0/s1
SMILES Code
CC(c1c(O)cc2c(CC[C@H]3C(C)(CCC[C@@]32C(O)=O)C)c1)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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
316.44
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: Aburai N, Yoshida M, Ohnishi M, Kimura K. Pisiferdiol and pisiferic acid isolated from Chamaecyparis pisifera activate protein phosphatase 2C in vitro and induce caspase-3/7-dependent apoptosis via dephosphorylation of Bad in HL60 cells. Phytomedicine. 2010 Aug;17(10):782-8. doi: 10.1016/j.phymed.2009.12.015. Epub 2010 Feb 12. PMID: 20153620.
2: Tada M, Ohkanda T, Kurabe J. Syntheses of carnosic acid and carnosol, anti- oxidants in Rosemary, from pisiferic acid, the major constituent of Sawara. Chem Pharm Bull (Tokyo). 2010 Jan;58(1):27-9. doi: 10.1248/cpb.58.27. PMID: 20045961.
3: Sadgrove NJ, Senbill H, Van Wyk BE, Greatrex BW. New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae). Antibiotics (Basel). 2020 Apr 11;9(4):173. doi: 10.3390/antibiotics9040173. PMID: 32290471; PMCID: PMC7235842.
4: Kang TH, Hwang EI, Yun BS, Shin CS, Kim SU. Chitin synthase 2 inhibitory activity of O-methyl pisiferic acid and 8,20-dihydroxy-9(11),13-abietadien-12-one, isolated from Chamaecyparis pisifera. Biol Pharm Bull. 2008 Apr;31(4):755-9. doi: 10.1248/bpb.31.755. PMID: 18379078.
5: Ignea C, Athanasakoglou A, Andreadelli A, Apostolaki M, Iakovides M, Stephanou EG, Makris AM, Kampranis SC. Overcoming the plasticity of plant specialized metabolism for selective diterpene production in yeast. Sci Rep. 2017 Aug 18;7(1):8855. doi: 10.1038/s41598-017-09592-5. PMID: 28821847; PMCID: PMC5562805.
6: Kobayashi K, Kuroda K, Shinomiya T, Nishino C, Ohya J, Sato S. Effect of pisiferic acid and its derivatives on cytotoxicity macromolecular synthesis and DNA polymerase alpha of HeLa cells. Int J Biochem. 1989;21(5):463-8. doi: 10.1016/0020-711x(89)90125-0. PMID: 2474465.
7: Lin S, Zhang YL, Liu MT, Zi JC, Gan ML, Song WX, Fan XN, Wang XN, Yang YC, Shi JG. Chemical constituents from branch of Fraxinus sieboldiana. Zhongguo Zhong Yao Za Zhi. 2015 Jul;40(13):2602-11. PMID: 26697686.
8: Aburai N, Yoshida J, Kobayashi M, Mizunuma M, Ohnishi M, Kimura K. Pisiferdiol restores the growth of a mutant yeast suffering from hyperactivated Ca2+ signalling through calcineurin inhibition. FEMS Yeast Res. 2013 Feb;13(1):16-22. doi: 10.1111/1567-1364.12003. Epub 2012 Sep 26. PMID: 23013541