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N-Hydroxypipecolic acid

Names

[ CAS No. ]:
115819-92-6

[ Name ]:
N-Hydroxypipecolic acid

[Synonym ]:
3,6-EPOXY-N-HYDROXY-1,2,3,6-TETRAHYDROPHTHALIMIDE
N-Hydroxy-DL-pipecolinsaeure
N-Hydroxy-1,4-epoxycyclohex-5-en-2,3-dicarboximid
2-hydroxy-3a,4,7,7a-tetrahydro-4,7-epioxido-isoindole-1,3-dione
N-Hydroxy-3,6-epoxy-1,2,3,6-tetrahydrophthalimide
1-hydroxy-piperidine-2-carboxylic acid
N-Hydroxy-1,4-epoxy-5-cyclohexene-2,3-dicarboximide
3,6-Epoxy-N-hydroxy

Biological Activity

[Description]:

N-Hydroxypipecolic acid (1-Hydroxy-2-piperidinecarboxylic acid), a plant metabolite and a systemic acquired resistance (SAR) regulator, orchestrates SAR establishment in concert with the immune signal salicylic acid. N-Hydroxypipecolic acid accumulates systemically in the plant foliage in response to pathogen attack. N-Hydroxypipecolic acid induces SAR to bacterial and oomycete infection[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[In Vitro]

The mode of action of N-Hydroxypipecolic acid (NHP) in SAR involves direct induction of SAR gene expression, signal amplification, priming for enhanced defense activation and positive interplay with salicylic acid signaling to ensure elevated plant immunity. Flavin-dependent-monooxygenase1 (FMO1) functions downstream of Pip by hydroxylating Pip to generate NHP[1][3].

[References]

[1]. Shan L, et al. Pipped at the Post: Pipecolic Acid Derivative Identified as SAR Regulator. Cell. 2018 Apr 5;173(2):286-287.

[2]. Ádám AL, et al. Signals of Systemic Immunity in Plants: Progress and Open Questions. Int J Mol Sci. 2018 Apr 10;19(4). pii: E1146.

[3]. Hartmann M, et al. N-hydroxypipecolic acid and salicylic acid: a metabolic duo for systemic acquired resistance. Curr Opin Plant Biol. 2019 Aug;50:44-57.

Chemical & Physical Properties

[ Molecular Formula ]:
C6H11NO3

[ Molecular Weight ]:
145.15600

[ Exact Mass ]:
145.07400

[ PSA ]:
60.77000

[ LogP ]:
0.25260

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds