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Prohydrojasmon

HCID 20056433
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Basic information

CAS
158474-72-7
Standard SMILES
CCCCC[C@H]1C(=O)CC[C@@H]1CC(=O)OCCC
InChIKey
IPDFPNNPBMREIF-CHWSQXEVSA-N
Molecular formula
C15H26O3
Average molar mass
254.36 g/mol
Monoisotopic mass
254.18819469

Overview

Prohydrojasmon is a member of Jasmonate derivatives. It is functionally related to a jasmonic acid.

Names & identifiers

Preferred name
Prohydrojasmon
IUPAC
propyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate
English name
Prohydrojasmon
Molecular formula
C15H26O3
Molecular weight
254.37

Names & synonyms

ProhydrojasmonProhydrojasmon [ISO]178602-66-9Prohydrojasmon [MI]Prohydrojasmon, (R)-FM8S3XXS8YNE65U4JM0FPropyl 2-((1R,2R)-3-oxo-2-pentylcyclopentyl)acetatepropyl dihydrojasmonateCyclopentaneacetic acid, 3-oxo-2-pentyl-, propyl ester, (1R,2R)-Cyclopentaneacetic acid, 3-oxo-2-pentyl-, propyl ester, (1R-trans)-Propyl dihydrojasmonate (Mixture of Diastereomers)
Show more names
PDJjasmonBlush PGRcas 158474-72-7Prohydrojasmon 5.25%Prohydrojasmon (PDJ)chemicalbookcheck CASProhydrojasmon racemate
UNII-NE65U4JM0FUNII-FM8S3XXS8YSCHEMBL119966propyl [(1r,2r)-3-oxo-2-pentylcyclopentyl]acetateProhydrojasmonmixture of isomersCHEBI:81814DTXSID801016600PROHYDROJASMON, (+/-)-

Database identifiers

CAS
158474-72-7、178602-66-9
PubChem CID
20056433
DTXSID
DTXSID801016600
ChEBI
CHEBI:81814
UNII
FM8S3XXS8Y、NE65U4JM0F
Nikkaji
J960.711K

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
9
Heavy atoms
18
Formal charge
0
Complexity
273

Experimental & physicochemical properties

Pesticides · 2 items

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Physicochemical properties

Boiling point
340.2 · 340.2±15.0 °C(Predicted)
Density
0.967 · 0.967±0.06 g/cm3(Predicted)
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)
form
Oil
color
Pale Yellow to Light Yellow
Henry's Law Constant
1.4 · 1.4×101 mol/(m3Pa) at 25℃, Ebert et al. (2023)
InChI
InChI=1S/C15H26O3/c1-3-5-6-7-13-12(8-9-14(13)16)11-15(17)18-10-4-2/h12-13H,3-11H2,1-2H3
InChIKey
IPDFPNNPBMREIF-UHFFFAOYSA-N
SMILES
C1(CC(OCCC)=O)CCC(=O)C1CCCCC
FDA UNII
65 U4JM0F · NE65U4JM0F

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H412-H319-H335-H315
Precautionary statements
P273-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications · 2 items

DescriptionProhydrojasmon (PDJ) [propyl(1RS,2RS)-(3-oxo-2-pentylcyclopentyl) acetate], an analog of Jasmonic acid (JA), was first registered as a plant growth regulator, particularly for coloring apples and grapes. Plant growth regulators are naturally or chemically synthesized substances that play roles in plants' developmental or metabolic processes. Subsequently, similar to JA, PDJ was found to induce direct and indirect defenses against herbivores in non-infested plants[1].

UsesProhydrojasmon (PDJ), as a plant growth regulator, focuses on fruits, including apples, oranges, mangoes, and grapes. Specifically, it has been applied to enhance mango and red pear fruit coloration. PDJ treatment of crops increases their direct and indirect defenses against several insect pests under open field conditions. A report on PDJ treatment of non-infested maize plants suggests a reduction in the weights and survival rates of the common armyworm, Mythimna separata (Walker), larvae and their increased attraction to Cotesia kariyai Watanabe, a parasitoid wasp of the herbivore. Furthermore, two-spotted spider mites (Tetranychus urticae Koch) laid significantly fewer eggs on PDJ-treated leaf disks than on control leaf disks. PDJ treatment of non-infested lima bean plants induced the production of volatiles, including (E)-β-ocimene and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), which attract Phytoseiulus persimilis Athias-Henriot, a predatory mite. Moreover, under greenhouse conditions, PDJ treatment of tomato plants negatively affects the damage caused by thrips[3].

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Compound notes

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EPA Substance Registry System
3 · Cyclopentaneacetic acid, 3-oxo-2-pentyl-, propyl ester (158474-72-7)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
412 · H412-H319-H335-H315
Precautionary statements
273 · P273-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P