Pinusolide | CAS#31685-80-0 | medicine

MedKoo Cat#: 145624 | Name: Pinusolide

Description:

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

Pinusolide is an herbal medicine isolated from Biota orientalis L. (B. orientalis). Pinusolide stimulates AMPK phosphorylation and glucose uptake. Pinusolide attenuates blockade of insulin signaling by enhancing IRS-1 tyrosine phosphorylation.

Chemical Structure

Pinusolide

CAS#31685-80-0

Theoretical Analysis

MedKoo Cat#: 145624

Name: Pinusolide

CAS#: 31685-80-0

Chemical Formula: C21H30O4

Exact Mass: 346.2100

Molecular Weight: 346.47

Elemental Analysis: C, 72.80; H, 8.73; O, 18.47

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

Pinusolide;

IUPAC/Chemical Name

methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylene-5-(2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl)decahydronaphthalene-1-carboxylate

InChi Key

WTKBZJAWPZXKJU-NLEAXPPASA-N

InChi Code

1S/C21H30O4/c1-14-6-9-17-20(2,11-5-12-21(17,3)19(23)24-4)16(14)8-7-15-10-13-25-18(15)22/h10,16-17H,1,5-9,11-13H2,2-4H3/t16-,17+,20+,21-/m0/s1

SMILES Code

[H][C@@]12CCC(=C)[C@H](CCC3=CCOC3=O)[C@@]1(C)CCC[C@]2(C)C(=O)OC

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 346.47 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: Jin Y, Yang HO, Son JK, Chang HW. Pinusolide isolated from Biota orientalis inhibits 5-lipoxygenase dependent leukotriene C4 generation by blocking c-Jun N-terminal kinase pathway in mast cells. Biol Pharm Bull. 2012;35(8):1374-8. doi: 10.1248/bpb.b12-00271. PMID: 22863941. 2: Hwang SL, Jeong YT, Hye Yang J, Li X, Lu Y, Son JK, Chang HW. Pinusolide improves high glucose-induced insulin resistance via activation of AMP-activated protein kinase. Biochem Biophys Res Commun. 2013 Aug 2;437(3):374-9. doi: 10.1016/j.bbrc.2013.06.084. Epub 2013 Jul 2. PMID: 23831466. 3: Kim KA, Moon TC, Lee SW, Chung KC, Han BH, Chang HW. Pinusolide from the leaves of Biota orientalis as potent platelet activating factor antagonist. Planta Med. 1999 Feb;65(1):39-42. doi: 10.1055/s-1999-13959. PMID: 10083843. 4: Koo KA, Lee MK, Kim SH, Jeong EJ, Kim SY, Oh TH, Kim YC. Pinusolide and 15-methoxypinusolidic acid attenuate the neurotoxic effect of staurosporine in primary cultures of rat cortical cells. Br J Pharmacol. 2007 Jan;150(1):65-71. doi: 10.1038/sj.bjp.0706944. Epub 2006 Dec 4. PMID: 17143305; PMCID: PMC2013848. 5: Choi Y, Moon A, Kim YC. A pinusolide derivative, 15-methoxypinusolidic acid from Biota orientalis inhibits inducible nitric oxide synthase in microglial cells: implication for a potential anti-inflammatory effect. Int Immunopharmacol. 2008 Apr;8(4):548-55. doi: 10.1016/j.intimp.2007.12.010. Epub 2008 Jan 16. PMID: 18328446. 6: Yang HO, Kang YH, Suh DY, Kim YC, Han BH. Biological and pharmacological effects of pinusolide, a novel platelet activating factor antagonist. Planta Med. 1995 Dec;61(6):519-22. doi: 10.1055/s-2006-959361. PMID: 8824945. 7: Negro Alvarez JM, Miralles López JC, Ortiz Martínez JL, Abellán Alemán A, Rubio del Barrio R. Platelet-activating factor antagonists. Allergol Immunopathol (Madr). 1997 Sep-Oct;25(5):249-58. PMID: 9395010. 8: Koo KA, Sung SH, Kim YC. A new neuroprotective pinusolide derivative from the leaves of Biota orientalis. Chem Pharm Bull (Tokyo). 2002 Jun;50(6):834-6. doi: 10.1248/cpb.50.834. PMID: 12045342. 9: Han BH, Yang HO, Kang YH, Suh DY, Go HJ, Song WJ, Kim YC, Park MK. In vitro platelet-activating factor receptor binding inhibitory activity of pinusolide derivatives: a structure-activity study. J Med Chem. 1998 Jul 2;41(14):2626-30. doi: 10.1021/jm970569j. PMID: 9651167. 10: Shults EE, Velder J, Schmalz HG, Chernov SV, Rubalova TV, Gatilov YV, Henze G, Tolstikov GA, Prokop A. Gram-scale synthesis of pinusolide and evaluation of its antileukemic potential. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4228-32. doi: 10.1016/j.bmcl.2006.05.077. Epub 2006 Jun 14. PMID: 16781150. 11: Wang A, Li Z, Wang J, Liu H, Fu X, Chen Y, Guo H. Quantification and holistic quality evaluation of Wulingzhi extract by UHPLC-Q-Orbitrap-HRMS coupled with chemometric approaches. Biomed Chromatogr. 2023 Nov;37(11):e5726. doi: 10.1002/bmc.5726. Epub 2023 Aug 31. PMID: 37651744. 12: Lee YS, Sung SH, Hong JH, Hwang ES. Suppression of adipocyte differentiation by 15-methoxypinusolidic acid through inhibition of PPARγ activity. Arch Pharm Res. 2010 Jul;33(7):1035-41. doi: 10.1007/s12272-010-0709-0. Epub 2010 Jul 27. PMID: 20661713. 13: Yan L, He X, Jin Y, Wang J, Liang F, Pei R, Li P, Wang Y, Su W. Modulation of the Aβ-Peptide-Aggregation Pathway by Active Compounds From Platycladus orientalis Seed Extract in Alzheimer's Disease Models. Front Aging Neurosci. 2020 Aug 14;12:207. doi: 10.3389/fnagi.2020.00207. PMID: 32922281; PMCID: PMC7456918. 14: Kim JY, Kim HJ, Kim SM, Park KR, Jang HJ, Lee EH, Jung SH, Ahn KS. Methylene chloride fraction of the leaves of Thuja orientalis inhibits in vitro inflammatory biomarkers by blocking NF-κB and p38 MAPK signaling and protects mice from lethal endotoxemia. J Ethnopharmacol. 2011 Jan 27;133(2):687-95. doi: 10.1016/j.jep.2010.10.051. Epub 2010 Oct 30. PMID: 21040769. 15: Yang HO, Suh DY, Han BH. Isolation and characterization of platelet- activating factor receptor binding antagonists from Biota orientalis. Planta Med. 1995 Feb;61(1):37-40. doi: 10.1055/s-2006-957995. PMID: 7700989. 16: Koo KA, Kim SH, Lee MK, Kim YC. 15-Methoxypinusolidic acid from Biota orientalis attenuates glutamate-induced neurotoxicity in primary cultured rat cortical cells. Toxicol In Vitro. 2006 Sep;20(6):936-41. doi: 10.1016/j.tiv.2006.02.001. Epub 2006 Feb 28. PMID: 16564156.