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MedKoo Cat#: 598242 | Name: Lambertianic acid

Description:

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

Lambertianic acid is a bioactive chemical that is known to have anti-allergic and antibacterial effects.

Chemical Structure

Lambertianic acid
Lambertianic acid
CAS#4966-13-6

Theoretical Analysis

MedKoo Cat#: 598242

Name: Lambertianic acid

CAS#: 4966-13-6

Chemical Formula: C20H28O3

Exact Mass: 316.2038

Molecular Weight: 316.44

Elemental Analysis: C, 75.91; H, 8.92; O, 15.17

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
Lambertianic acid;
IUPAC/Chemical Name
methyl (1S,4aR,5S,8aR)-5-(2-(furan-3-yl)ethyl)-4a-methyl-6-methylenedecahydronaphthalene-1-carboxylate
InChi Key
XZOUFGJMCGQXNM-GNBUJSLZSA-N
InChi Code
InChI=1S/C20H28O3/c1-14-6-8-18-16(19(21)22-3)5-4-11-20(18,2)17(14)9-7-15-10-12-23-13-15/h10,12-13,16-18H,1,4-9,11H2,2-3H3/t16-,17-,18+,20-/m0/s1
SMILES Code
C[C@@]1([C@H](CC2)[C@@H](C(OC)=O)CCC1)[C@@H](CCc3ccoc3)C2=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
2934.99.03.00
More Info

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.

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: Avgustinovich DF, Fomina MK, Sorokina IV, Tolstikova TG. Complex investigation of the effects of lambertianic acid amide in female mice under conditions of social discomfort. Bull Exp Biol Med. 2014 Sep;157(5):583-7. doi: 10.1007/s10517-014-2621-y. Epub 2014 Sep 26. PubMed PMID: 25257419. 2: Chae HS, Chin YW. Anti-allergic effect of lambertianic acid from Thuja orientalis in mouse bone marrow-derived mast cells. Immunopharmacol Immunotoxicol. 2012 Apr;34(2):250-5. doi: 10.3109/08923973.2011.600763. Epub 2011 Aug 19. PubMed PMID: 21854102. 3: Lee MS, Lee SO, Kim SH, Lee EO, Lee HJ. Anti-Cancer Effect of Lambertianic Acid by Inhibiting the AR in LNCaP Cells. Int J Mol Sci. 2016 Jul 7;17(7). pii: E1066. doi: 10.3390/ijms17071066. PubMed PMID: 27399684; PubMed Central PMCID: PMC4964442. 4: Lee MS, Cho SM, Lee MH, Lee EO, Kim SH, Lee HJ. Ethanol extract of Pinus koraiensis leaves containing lambertianic acid exerts anti-obesity and hypolipidemic effects by activating adenosine monophosphate-activated protein kinase (AMPK). BMC Complement Altern Med. 2016 Feb 4;16:51. doi: 10.1186/s12906-016-1031-2. PubMed PMID: 26846328; PubMed Central PMCID: PMC4743410. 5: Vechkapova SO, Zapara TA, Morozova EA, Proskura AL, Schul'ts EE, Tolstikova TG, Ratushnyak AS. Amide of Lambertian Acid Suppresses Hyperactivation of Inotropic Glutamate Receptors, but not Synaptic Potentiation in Hippocampal Sections. Bull Exp Biol Med. 2016 Oct;161(6):782-785. Epub 2016 Oct 26. PubMed PMID: 27783303. 6: Yang X, Ding Y, Sun ZH, Zhang DM. [Studies on chemical constituents of Pinus armandii]. Yao Xue Xue Bao. 2005 May;40(5):435-7. Chinese. PubMed PMID: 16220788. 7: Cota BB, de Oliveira DM, de Siqueira EP, Souza-Fagundes EM, Pimenta AM, Santos DM, Rabello A, Zani CL. New cassane diterpenes from Caesalpinia echinata. Fitoterapia. 2011 Oct;82(7):969-75. doi: 10.1016/j.fitote.2011.05.014. Epub 2011 May 27. PubMed PMID: 21641971. 8: Tolstikova TG, Voevoda TV, Dolgikh MP, Sorokina IV. [Neurotropic activity of lambertian acid and its amino derivatives]. Eksp Klin Farmakol. 2002 Mar-Apr;65(2):9-11. Russian. PubMed PMID: 12109303. 9: Yang X, Zhang YC, Zhang H, Wang J. [Isolation and identification of diterpenoids from Pinus koraiensis]. Zhong Yao Cai. 2008 Jan;31(1):53-5. Chinese. PubMed PMID: 18589751. 10: 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. PubMed PMID: 12045342. 11: 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. Epub 2006 Jun 14. PubMed PMID: 16781150. 12: Kharitonov IuV, Shul'ts ÉÉ, Shakirov MM, Pokrovskiĭ MA, Pokrovskiĭ AG, Tolstikov GA. [Synthetic transformations of higher terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and theirs cytotoxicity]. Bioorg Khim. 2012 Jan-Feb;38(1):127-36. Russian. PubMed PMID: 22792716. 13: Jeong A, Kim JH, Lee HJ, Kim SH. Reactive oxygen species dependent phosphorylation of the liver kinase B1/AMP activated protein kinase/ acetyl-CoA carboxylase signaling is critically involved in apoptotic effect of lambertianic acid in hepatocellular carcinoma cells. Oncotarget. 2017 Jul 26;8(41):70116-70129. doi: 10.18632/oncotarget.19592. eCollection 2017 Sep 19. PubMed PMID: 29050265; PubMed Central PMCID: PMC5642540. 14: Tolstikova TG, Dolgikh MP, Tolstikov GA. Lambertian acid and its amino derivatives: a new group of perspective neurotropic agents. Dokl Biol Sci. 2000 Sep-Oct;374:445-7. PubMed PMID: 11103310. 15: Lee JH, Lee HJ, Sim DY, Jung JH, Kim KR, Kim SH. Apoptotic effect of lambertianic acid through AMPK/FOXM1 signaling in MDA-MB231 breast cancer cells. Phytother Res. 2018 May 2. doi: 10.1002/ptr.6105. [Epub ahead of print] PubMed PMID: 29722086. 16: Ahn DS, Lee HJ, Hwang J, Han H, Kim B, Shim B, Kim SH. Lambertianic Acid Sensitizes Non-Small Cell Lung Cancers to TRAIL-Induced Apoptosis via Inhibition of XIAP/NF-κB and Activation of Caspases and Death Receptor 4. Int J Mol Sci. 2018 May 16;19(5). pii: E1476. doi: 10.3390/ijms19051476. PubMed PMID: 29772677; PubMed Central PMCID: PMC5983579. 17: Shpatov AV, Popov SA, Salnikova OI, Kukina TP, Shmidt EN, Um BH. Composition and Bioactivity of Lipophilic Metabolites from Needles and Twigs of Korean and Siberian Pines (Pinus koraiensis Siebold & Zucc. and Pinus sibirica Du Tour). Chem Biodivers. 2017 Feb;14(2). doi: 10.1002/cbdv.201600203. Epub 2017 Feb 4. PubMed PMID: 27449469.

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GSK1723980

GSK1723980