12-Oxo-Phytodienoic acid | CAS#85551-10-6 | endogenous signal transducer

MedKoo Cat#: 561523 | Name: 12-Oxo-Phytodienoic acid

Description:

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

12-Oxo-Phytodienoic acid, also known as OPDA, or 12-oxo PDA, is a plant-derived oxylipin and an endogenous signal transducer. OPDA attenuates lipopolysaccharide-induced inflammation in microglia. OPDA represses Arabidopsis seed germination in shade conditions. OPDA acts as a Regulator of Maize Defense against Corn Leaf Aphid. OPDA Enhances Wheat Resistance to Hessian Fly (Diptera: Cecidomyiidae) Under Heat Stress. Note: This product is supplied as a pre-dissolved solution in ethanol (10 mL/mL).

Chemical Structure

12-Oxo-Phytodienoic acid

CAS#85551-10-6

Theoretical Analysis

MedKoo Cat#: 561523

Name: 12-Oxo-Phytodienoic acid

CAS#: 85551-10-6

Chemical Formula: C18H28O3

Exact Mass: 292.2038

Molecular Weight: 292.41

Elemental Analysis: C, 73.93; H, 9.65; O, 16.41

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

12-Oxo-Phytodienoic acid; 12-oxo PDA; OPDA; 12-oxo Phytodienoic Acid;

IUPAC/Chemical Name

8-((1S,5S)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)octanoic acid

InChi Key

PMTMAFAPLCGXGK-JMTMCXQRSA-N

InChi Code

InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1

SMILES Code

O=C(O)CCCCCCC[C@H]1C=CC([C@H]1C/C=C\CC)=O

Appearance

Oily liquid

Purity

chemical purity > 90%, optical pure>70%.

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, ethanol.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in ethanol

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

Certificate of Analysis

View CoA: current batch, Lot#YXM91127

QC Data

View QC data: current batch, Lot#YXM91127

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 292.41 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: Barros-Galvão T, Dave A, Cole A, Harvey D, Langer S, Larson TR, Vaistij FE, Graham IA. cis-12-Oxo-phytodienoic acid represses Arabidopsis seed germination in shade conditions. J Exp Bot. 2019 Oct 24;70(20):5919-5927. doi: 10.1093/jxb/erz337. PubMed PMID: 31326997; PubMed Central PMCID: PMC6812700. 2: Varsani S, Grover S, Zhou S, Koch KG, Huang PC, Kolomiets MV, Williams WP, Heng-Moss T, Sarath G, Luthe DS, Jander G, Louis J. 12-Oxo-Phytodienoic Acid Acts as a Regulator of Maize Defense against Corn Leaf Aphid. Plant Physiol. 2019 Apr;179(4):1402-1415. doi: 10.1104/pp.18.01472. Epub 2019 Jan 14. PubMed PMID: 30643012; PubMed Central PMCID: PMC6446797. 3: Enomoto H, Sensu T, Yumoto E, Yokota T, Yamane H. Derivatization for detection of abscisic acid and 12-oxo-phytodienoic acid using matrix-assisted laser desorption/ionization imaging mass spectrometry. Rapid Commun Mass Spectrom. 2018 Sep 15;32(17):1565-1572. doi: 10.1002/rcm.8200. PubMed PMID: 29888502. 4: Uchiyama A, Yaguchi T, Nakagawa H, Sasaki K, Kuwata N, Matsuura H, Takahashi K. Biosynthesis and in vitro enzymatic synthesis of the isoleucine conjugate of 12-oxo-phytodienoic acid from the isoleucine conjugate of α-linolenic acid. Bioorg Med Chem Lett. 2018 Apr 1;28(6):1020-1023. doi: 10.1016/j.bmcl.2018.02.030. Epub 2018 Feb 15. PubMed PMID: 29486965. 5: Cheng G, Chen MS, Zhu L. 12-Oxo-Phytodienoic Acid Enhances Wheat Resistance to Hessian Fly (Diptera: Cecidomyiidae) Under Heat Stress. J Econ Entomol. 2018 Apr 2;111(2):917-922. doi: 10.1093/jee/tox374. PubMed PMID: 29420735. 6: Cheong H, Barbosa Dos Santos I, Liu W, Gosse HN, Park SW. Cyclophilin 20-3 is positioned as a regulatory hub between light-dependent redox and 12-oxo-phytodienoic acid signaling. Plant Signal Behav. 2017 Sep 2;12(9):e1362520. doi: 10.1080/15592324.2017.1362520. Epub 2017 Aug 14. PubMed PMID: 28805482; PubMed Central PMCID: PMC5640192. 7: Enomoto H, Sensu T, Sato K, Sato F, Paxton T, Yumoto E, Miyamoto K, Asahina M, Yokota T, Yamane H. Visualisation of abscisic acid and 12-oxo-phytodienoic acid in immature Phaseolus vulgaris L. seeds using desorption electrospray ionisation-imaging mass spectrometry. Sci Rep. 2017 Feb 17;7:42977. doi: 10.1038/srep42977. PubMed PMID: 28211480; PubMed Central PMCID: PMC5314351. 8: Meza-Canales ID, Meldau S, Zavala JA, Baldwin IT. Herbivore perception decreases photosynthetic carbon assimilation and reduces stomatal conductance by engaging 12-oxo-phytodienoic acid, mitogen-activated protein kinase 4 and cytokinin perception. Plant Cell Environ. 2017 Jul;40(7):1039-1056. doi: 10.1111/pce.12874. Epub 2017 Mar 27. PubMed PMID: 27925291. 9: Arnold MD, Gruber C, Floková K, Miersch O, Strnad M, Novák O, Wasternack C, Hause B. The Recently Identified Isoleucine Conjugate of cis-12-Oxo-Phytodienoic Acid Is Partially Active in cis-12-Oxo-Phytodienoic Acid-Specific Gene Expression of Arabidopsis thaliana. PLoS One. 2016 Sep 9;11(9):e0162829. doi: 10.1371/journal.pone.0162829. eCollection 2016. PubMed PMID: 27611078; PubMed Central PMCID: PMC5017875. 10: Luo W, Nanjo Y, Komatsu S, Matsuura H, Takahashi K. Proteomics of Physcomitrella patens protonemata subjected to treatment with 12-oxo-phytodienoic acid. Biosci Biotechnol Biochem. 2016 Dec;80(12):2357-2364. Epub 2016 Aug 25. PubMed PMID: 27558085. 11: Nilsson AK, Fahlberg P, Johansson ON, Hamberg M, Andersson MX, Ellerström M. The activity of HYDROPEROXIDE LYASE 1 regulates accumulation of galactolipids containing 12-oxo-phytodienoic acid in Arabidopsis. J Exp Bot. 2016 Sep;67(17):5133-44. doi: 10.1093/jxb/erw278. Epub 2016 Jul 15. PubMed PMID: 27422994; PubMed Central PMCID: PMC5014160. 12: Taki-Nakano N, Kotera J, Ohta H. 12-oxo-phytodienoic acid, a plant-derived oxylipin, attenuates lipopolysaccharide-induced inflammation in microglia. Biochem Biophys Res Commun. 2016 May 13;473(4):1288-1294. doi: 10.1016/j.bbrc.2016.04.060. Epub 2016 Apr 14. PubMed PMID: 27086850. 13: Dave A, Vaistij FE, Gilday AD, Penfield SD, Graham IA. Regulation of Arabidopsis thaliana seed dormancy and germination by 12-oxo-phytodienoic acid. J Exp Bot. 2016 Apr;67(8):2277-84. doi: 10.1093/jxb/erw028. Epub 2016 Feb 11. PubMed PMID: 26873978; PubMed Central PMCID: PMC4809285. 14: Wang Y, Yuan G, Yuan S, Duan W, Wang P, Bai J, Zhang F, Gao S, Zhang L, Zhao C. TaOPR2 encodes a 12-oxo-phytodienoic acid reductase involved in the biosynthesis of jasmonic acid in wheat (Triticum aestivum L.). Biochem Biophys Res Commun. 2016 Jan 29;470(1):233-238. doi: 10.1016/j.bbrc.2016.01.043. Epub 2016 Jan 9. PubMed PMID: 26778003. 15: Król P, Igielski R, Pollmann S, Kępczyńska E. Priming of seeds with methyl jasmonate induced resistance to hemi-biotroph Fusarium oxysporum f.sp. lycopersici in tomato via 12-oxo-phytodienoic acid, salicylic acid, and flavonol accumulation. J Plant Physiol. 2015 May 1;179:122-32. doi: 10.1016/j.jplph.2015.01.018. Epub 2015 Mar 14. PubMed PMID: 25867625. 16: Cassin-Ross G, Hu J. A simple assay to identify peroxisomal proteins involved in 12-oxo-phytodienoic acid metabolism. Plant Signal Behav. 2014;9(8):e29464. doi: 10.4161/psb.29464. PubMed PMID: 25763626; PubMed Central PMCID: PMC4203641. 17: Guo HM, Li HC, Zhou SR, Xue HW, Miao XX. Cis-12-oxo-phytodienoic acid stimulates rice defense response to a piercing-sucking insect. Mol Plant. 2014 Nov;7(11):1683-1692. doi: 10.1093/mp/ssu098. Epub 2014 Sep 19. PubMed PMID: 25239066. 18: Taki-Nakano N, Ohzeki H, Kotera J, Ohta H. Cytoprotective effects of 12-oxo phytodienoic acid, a plant-derived oxylipin jasmonate, on oxidative stress-induced toxicity in human neuroblastoma SH-SY5Y cells. Biochim Biophys Acta. 2014 Dec;1840(12):3413-22. doi: 10.1016/j.bbagen.2014.09.003. Epub 2014 Sep 16. PubMed PMID: 25219458. 19: Masuda S, Tokaji Y, Kobayashi Y, Ohta H. Mechanisms of induction of the stress-responsive transcription factors HsfA2 and DREB2A by 12-oxo-phytodienoic acid in Arabidopsis thaliana. Biosci Biotechnol Biochem. 2014;78(4):647-50. doi: 10.1080/09168451.2014.891929. Epub 2014 Apr 29. PubMed PMID: 25036962. 20: Toshima E, Nanjo Y, Komatsu S, Abe T, Matsuura H, Takahashi K. Proteomic analysis of Physcomitrella patens treated with 12-oxo-phytodienoic acid, an important oxylipin in plants. Biosci Biotechnol Biochem. 2014;78(6):946-53. doi: 10.1080/09168451.2014.912112. Epub 2014 May 28. PubMed PMID: 25036118.