Synonym
Tuberonic acid; 12-OH-JA; (-)-12-hydroxyjasmonic acid; (1R,2R)-12-Hydroxyjasmonic acid; 12-Hydroxyjasmonic acid
IUPAC/Chemical Name
{(1R,2R)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl}acetic acid
InChi Key
RZGFUGXQKMEMOO-BSANDHCLSA-N
InChi Code
InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10-/m1/s1
SMILES Code
O=C(O)C[C@@H]1[C@@H](C/C=C\CCO)C(CC1)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
226.27
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: Arens N, Backhaus A, Döll S, Fischer S, Seiffert U, Mock HP. Non-invasive Presymptomatic Detection of Cercospora beticola Infection and Identification of Early Metabolic Responses in Sugar Beet. Front Plant Sci. 2016 Sep 22;7:1377. eCollection 2016. PubMed PMID: 27713750; PubMed Central PMCID: PMC5031787.
2: Widemann E, Miesch L, Lugan R, Holder E, Heinrich C, Aubert Y, Miesch M, Pinot F, Heitz T. The amidohydrolases IAR3 and ILL6 contribute to jasmonoyl-isoleucine hormone turnover and generate 12-hydroxyjasmonic acid upon wounding in Arabidopsis leaves. J Biol Chem. 2013 Nov 1;288(44):31701-14. doi: 10.1074/jbc.M113.499228. Epub 2013 Sep 19. PubMed PMID: 24052260; PubMed Central PMCID: PMC3814765.
3: Seto Y, Hamada S, Ito H, Masuta C, Matsui H, Nabeta K, Matsuura H. Tobacco salicylic acid glucosyltransferase is active toward tuberonic acid (12-hydroxyjasmonic acid) and is induced by mechanical wounding stress. Biosci Biotechnol Biochem. 2011;75(12):2316-20. Epub 2011 Dec 7. PubMed PMID: 22146717.
4: Nakamura Y, Mithöfer A, Kombrink E, Boland W, Hamamoto S, Uozumi N, Tohma K, Ueda M. 12-hydroxyjasmonic acid glucoside is a COI1-JAZ-independent activator of leaf-closing movement in Samanea saman. Plant Physiol. 2011 Mar;155(3):1226-36. doi: 10.1104/pp.110.168617. Epub 2011 Jan 12. PubMed PMID: 21228101; PubMed Central PMCID: PMC3046581.
