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MedKoo Cat#: 591408 | Name: Agathic acid

Description:

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

Agathic acid metabolite of isocupressic acid.

Chemical Structure

Agathic acid
Agathic acid
CAS#640-28-8

Theoretical Analysis

MedKoo Cat#: 591408

Name: Agathic acid

CAS#: 640-28-8

Chemical Formula: C20H30O4

Exact Mass: 334.2144

Molecular Weight: 334.46

Elemental Analysis: C, 71.82; H, 9.04; O, 19.13

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
Agathic acid;
IUPAC/Chemical Name
(1R,4aS,5R,8aR)-5-((E)-4-carboxy-3-methylbut-3-en-1-yl)-1,4a-dimethyl-6-methylenedecahydronaphthalene-1-carboxylic acid
InChi Key
QYCOHMYDSOZCQD-ITMPRHFASA-N
InChi Code
InChI=1S/C20H30O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h12,15-16H,2,5-11H2,1,3-4H3,(H,21,22)(H,23,24)/b13-12+/t15-,16-,19+,20-/m1/s1
SMILES Code
O=C([C@]1(C)CCC[C@]2(C)[C@H]1CCC([C@H]2CC/C(C)=C/C(O)=O)=C)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

Preparing Stock Solutions

The following data is based on the product molecular weight 334.46 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: Kamdem RST, Wang H, Wafo P, Ebrahim W, Özkaya FC, Makhloufi G, Janiak C, Sureechatchaiyan P, Kassack MU, Lin W, Liu Z, Proksch P. Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture. Fitoterapia. 2018 Jan;124:132-136. doi: 10.1016/j.fitote.2017.10.021. Epub 2017 Oct 26. PubMed PMID: 29106994. 2: Welch KD, Stonecipher CA, Gardner DR, Cook D, Pfister JA. Changes in the rumen bacterial microbiome of cattle exposed to ponderosa pine needles. J Anim Sci. 2017 May;95(5):2314-2322. doi: 10.2527/jas.2016.1228. PubMed PMID: 28727013. 3: Nohra YA, Perrichot V, Jeanneau L, Le Pollès L, Azar D. Chemical Characterization and Botanical Origin of French Ambers. J Nat Prod. 2015 Jun 26;78(6):1284-93. doi: 10.1021/acs.jnatprod.5b00093. Epub 2015 Jun 12. PubMed PMID: 26070107. 4: Snider DB, Gardner DR, Janke BH, Ensley SM. Pine needle abortion biomarker detected in bovine fetal fluids. J Vet Diagn Invest. 2015 Jan;27(1):74-9. doi: 10.1177/1040638714554443. Epub 2014 Nov 26. PubMed PMID: 25428187. 5: Shapiro D, Deering-Rice CE, Romero EG, Hughen RW, Light AR, Veranth JM, Reilly CA. Activation of transient receptor potential ankyrin-1 (TRPA1) in lung cells by wood smoke particulate material. Chem Res Toxicol. 2013 May 20;26(5):750-8. doi: 10.1021/tx400024h. Epub 2013 Apr 25. PubMed PMID: 23541125; PubMed Central PMCID: PMC3670828. 6: Welch KD, Gardner DR, Pfister JA, Panter KE, Zieglar J, Hall JO. A comparison of the metabolism of the abortifacient compounds from Ponderosa pine needles in conditioned versus naive cattle. J Anim Sci. 2012 Dec;90(12):4611-7. doi: 10.2527/jas.2012-5232. Epub 2012 Jun 13. PubMed PMID: 22696617. 7: Kimura K, Minamikawa Y, Ogasawara Y, Yoshida J, Saitoh K, Shinden H, Ye YQ, Takahashi S, Miyakawa T, Koshino H. Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay. Fitoterapia. 2012 Jul;83(5):907-12. doi: 10.1016/j.fitote.2012.03.024. Epub 2012 Apr 2. PubMed PMID: 22507387. 8: Gardner DR, Panter KE, Stegelmeier BL. Implication of agathic acid from Utah juniper bark as an abortifacient compound in cattle. J Appl Toxicol. 2010 Mar;30(2):115-9. doi: 10.1002/jat.1476. PubMed PMID: 19757408. 9: Park YC, Gunasekera SP, Lopez JV, McCarthy PJ, Wright AE. Metabolites from the marine-derived fungus Chromocleista sp. isolated from a deep-water sediment sample collected in the Gulf of Mexico. J Nat Prod. 2006 Apr;69(4):580-4. PubMed PMID: 16643030. 10: Lee ST, Gardner DR, Garrosian M, Panter KE, Serrequi AN, Schoch TK, Stegelmeier BL. Development of enzyme-linked immunosorbent assays for isocupressic acid and serum metabolites of isocupressic acid. J Agric Food Chem. 2003 May 21;51(11):3228-33. PubMed PMID: 12744647. 11: Garrossian M, Gardner DR, Panter KE, James LF. Preparation of tetrahydroagathic acid: a serum metabolite of isocupressic acid, a cattle abortifacient in ponderosa pine. J Agric Food Chem. 2002 Apr 10;50(8):2235-40. PubMed PMID: 11929277. 12: Gardner DR, Panter KE, James LF. Pine needle abortion in cattle: metabolism of isocupressic acid. J Agric Food Chem. 1999 Jul;47(7):2891-7. PubMed PMID: 10552582. 13: Lin SJ, Short RE, Ford SP, Grings EE, Rosazza JP. In vitro biotransformations of isocupressic acid by cow rumen preparations: formation of agathic and dihydroagathic acids. J Nat Prod. 1998 Jan;61(1):51-6. PubMed PMID: 9461652. 14: TAHARA A, HOSHINO O, HAMAZAKI Y. NEW INTER-RELATIONSHIP OF ABIETIC ACID AND AGATHIC ACID. Chem Pharm Bull (Tokyo). 1963 Oct;11:1328-31. PubMed PMID: 14075290.