Methyl 3-oxo-2-(2-penten-1-yl)cyclopentaneacetate

224.30

224.14124450

243-497-1|214-918-6|254-705-5

DTXSID3036731

Colorless liquid

log Kow = 2.76 (est)

Specific density: 1.021 at 22.6 °C/4 °C|1.017-1.023

BP: 110 °C at 0.2 mm Hg

> 113 degrees C (> 235 degrees F) - closed cup

Index of refraction: 1.4730 at 21.8 °C/D|1.470-1.476

In water, 340 mg/L at 25 °C (est)|Soluble in oils; Slightly soluble in water|Soluble (in ethanol)

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

3.37X10-4 mm Hg at 25 °C (est)

Sharp persistent odor

Henry's Law constant = 1.38X10-8 atm-cu m/mol at 25 °C (est)

Colorless oil. Index of refraction: 1.486 at 23 °C/D. Specific optical rotation: -73 deg at 25 °C/D (concn = 1 in CH3OH) /Jasmonic acid/|Hydroxyl radical reaction rate constant = 7.39X10-12 cu cm/mole-sec (cis); 8.15X10-12 cu cm/molec-sec (trans), both at 25 °C (est)|Ozone radical reaction rate constant = 1.3X10-16 cu cm/mole-sec (cis); 2.0X10-16 cu cm/molec-sec (trans), at 25 °C (est)

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 210 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Respiratory protection/:/ Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Hand protection/:/ Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Eye protection Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin and body protection /:/ Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.

/Investigators/ studied the effects of methyl jasmonate in combination with sucrose on defense-related gene expression, stilbene and anthocyanin production in grapevine cell suspensions. The methyl jasmonate/sucrose treatment was effective in stimulating phenylalanine ammonia lyase, chalcone synthase, stilbene synthase, UDP-glucose: flavonoid-O-glucosyltransferase, proteinase inhibitor and chitinase gene expression, and triggered accumulation of both piceids and anthocyanins in cells, and trans-resveratrol and piceids in the extracellular medium...|Capsicum annuum /(C. annuum)/ suspension cell cultures were used to evaluate the effect of cyclodextrins and methyl jasmonate as elicitors of defense responses. The induced defense responses included the accumulation of sesquiterpenes and phytosterols and the activation of pathogenesis-related proteins, leading to reinforcement and modification of the cell wall architecture during elicitation and protection cells against biotic stress. The results showed that the addition of both cyclodextrins and methyl jasmonate induced the biosynthesis of two sesquiterpenes, aromadendrene and solavetivone. This response was clearly synergistic since the increase in the levels of these compounds was much greater in the presence of both elicitors than when they were used separately. The biosynthesis of phytosterols was also induced in the combined treatment, as the result of an additive effect. Likewise, the exogenous application of methyl jasmonate induced the accumulation of pathogenesis-related proteins. The analysis of the extracellular proteome showed the presence of amino acid sequences homologous to PR1 and 4, NtPRp27-like proteins and class I chitinases, peroxidases and the hydrolytic enzymes LEXYL1 and 2, arabinosidases, pectinases, nectarin IV and leucin-rich repeat protein, which suggests that methyl jasmonate plays a role in mediating defense-related gene product expression in C. annuum. Apart from these methyl jamonate-induced proteins, other PR proteins were found in both the control and elicited cell cultures of C. annuum. These included class IV chitinases, beta-1,3-glucanases, thaumatin-like proteins and peroxidases, suggesting that their expression is mainly constitutive since they are involved in growth, development and defense processes.|Boron is an essential plant micronutrient, but it is phytotoxic if present in excessive amounts in soil for certain plants such as Artemisia annua L. /(A. annua)/ that contains artemisinin (an important antimalarial drug) in its areal parts. Artemisinin is a sesquiterpene lactone with an endoperoxide bridge... the present research was conducted to determine whether the exogenous application of methyl jasmonate (MeJA) could combat the ill effects of excessive /Boron stress/ (B) present in the soil. According to the results obtained, the B toxicity induced oxidative stress and reduced the stem height as well as fresh and dry masses of the plant remarkably. The excessive amounts of soil B also lowered the net photosynthetic rate, stomatal conductance, internal CO2 concentration and total chlorophyll content in the leaves. In contrast, the foliar application of MeJA enhanced the growth and photosynthetic efficiency both in the stressed and non-stressed plants. The excessive B levels also increased the activities of antioxidant enzymes, such as catalase, peroxidase and superoxide dismutase... the MeJA application to the stressed plants reduced the amount of lipid peroxidation and stimulated the synthesis of antioxidant enzymes, enhancing the content and yield of artemisinin as well. Thus, it was concluded that MeJA might be utilized in mitigating the B toxicity and improving the content and yield of artemisinin in A. annua plant.

/PLANTS/ In the vicinity of big sagebrush (Artemisia tridentata), the growth of Nicotiana attenuata is negatively affected, in part due to the alleopathic effect of methyl jasmonate (MeJA) which is produced in large quantities by the aerial parts of sagebrush. Preliminary experiments suggested that growth-inhibiting substances were being emitted from the sagebrush roots... Fractions rich in volatile compounds were particularly phytotoxic. /Investigators/ analyzed the volatiles emitted from the roots of intact Artemisia tridentata plants grown in soil, sand, and hydroponic cultures by using dynamic headspace extraction, headspace solvent-microextraction (HSME) and headspace solid-phase microextraction (HSPME), and GC-MS. Camphor, 1,8-cineol, nerol, and neryl isovalerate were phytotoxic and released as the major constituents. In addition to the phytotoxic monoterpenes, himachalenes, longifolene, caryophyllene, and acetylenic spiroethers, were found as characteristic components in the root's volatiles. The allelopathic potential of these root volatiles was compared with that of methyl jasmonate (MeJA), one of the most active compounds emitted from above-ground parts of the plant.

Methyl jasmonate is a volatile component of the flowers of Jasmin, Jasminum officinale(1) and Japanese honeysuckle (Lonicera japonica)(2).|Originally isolayted from jasmin flowers ...|Naturally occuring plant growth inhibitor. /Jasmonic acid/

Methyl jasmonate's production and use in food safety research(1) and in traditional Chinese medicine(2) may result in its release to the environment through various waste streams(SRC); its use in perfumes(3) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that methyl jasmonate is expected to have high mobility in soil(SRC). Volatilization of methyl jasmonate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Methyl jasmonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2013).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that methyl jasmonate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 31(SRC), from an estimated log Kow of 2.76(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is not expected to be an important environmental fate process based on estimated hydrolysis half-lives of 12.3, 1,2 years and 44 days at pH values of 7,8 and 9, respectively(7). Biodegradation data in water were not available(SRC, 2013).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl jasmonate, which has an estimated vapor pressure of 3.4X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl jasmonate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-lives for these reactions in air are estimated to be 2.1 and 3.1 hours for the cis- and trans-isomers, respectively(SRC), calculated from its rate constant of 7.4X10-12 (cis-) and 8.2X10-12 (trans-isomer) cu cm/molecule-sec at 25 °C(SRC) that were derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of methyl jasmonate with ozone has been estimated as 1.3X10-16 (cis-isomer) and 2.0X10-16 (trans-isomer) cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to atmospheric half-lives of about 2.1 and 1.3 hrs, for the cis- and trans-isomers, respectively, at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Particulate-phase methyl jasmonate may be removed from the air by wet and dry deposition(SRC). Methyl jasmonate contains chromophores that absorb at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of methyl jasmonate with photochemically-produced hydroxyl radicals have been estimated as 7.4X10-12 and 7.2X10-12 cu cm/molecule-sec for the cis- and trans-isomers, respectively, at 25 °C(SRC) using a structure estimation method(1). This corresponds to atmospheric half-lives of about 1.7 (cis-isomer) and 1.6 (trans-isomer) hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constants for the vapor-phase reaction of methyl jasmonate with ozone have been estimated as 1.3X10-16 (cis-isomer) and 2.0X10-16 (trans-isomer) cu cm/molecule-sec at 25 °C(SRC) that were derived using a structure estimation method(1). These correspond to atmospheric half-lives of about 2.1 and 1.3 hrs, for the cis- and trans-isomers, respectively, at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 1.8X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 12.3, 1.2 yrs and 44 days at pH values of 7, 8 and 9, respectively(3). Methyl jasmonate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 31 was calculated in fish for methyl jasmonate(SRC), using an estimated log Kow of 2.76(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of methyl jasmonate can be estimated to be 150(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl jasmonate is expected to have high mobility in soil.

The Henry's Law constant for methyl jasmonate is estimated as 1.4X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl jasmonate is expected to be essentially nonvolatile from water surfaces(2). Methyl jasmonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to methyl jasmonate may occur through inhalation and dermal contact with this compound at workplaces where methyl jasmonate is produced or used. Use data indicate that the general population may be exposed to methyl jasmonate via inhalation, ingestion and dermal contact with consumer products containing methyl jasmonate. (SRC)

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)

Using the tomato pathotype of Alternaria alternata (Aa) and its AAL-toxin/tomato interaction as a model system, /the authors/ demonstrate a possible role for /jasmonic acid/ JA in susceptibility of plants against pathogens, which utilize host-specific toxins as virulence effectors. Disease development and in planta growth of the tomato pathotype of Aa were decreased in the def1 mutant, defective in biosynthesis of JA, compared with the wild-type (WT) cultivar. Exogenous methyl jasmonate (MeJA) application restored pathogen disease symptoms to the def1 mutant and led to increased disease in the WT. On the other hand, necrotic cell death was similarly induced by AAL-toxin both on def1 and WT, and MeJA application to the tomatoes did not affect the degree of cell death by the toxin. These results indicate that the JA-dependent signaling pathway is not involved in host basal defense responses against the tomato pathotype of Aa, but rather might affect pathogen acceptability via a toxin-independent manner. Data further suggest that JA has a promotional effect on susceptibility of tomato to toxigenic and necrotrophic pathogens, such that pathogens might utilize the JA signaling pathway for successful infection.|...WRKY plant-specific transcription factors, as one of the flagellin-inducible genes in /its non-host/ A. thaliana. Expression of WRKY41 is induced by inoculation with the incompatible pathogen P. syringae pv. tomato DC3000 (Pto) possessing AvrRpt2 and the non-host pathogens... Arabidopsis overexpressing WRKY41 showed enhanced resistance to the Pto wild-type but increased susceptibility to Erwinia carotovora EC1. WRKY41-overexpressing Arabidopsis constitutively expresses the PR5 gene, but suppresses the methyl jasmonate-induced PDF1.2 gene expression. These results demonstrate that WRKY41 may be a key regulator in the cross talk of salicylic acid and jasmonic acid pathways.|Induction of cell death is an important component of plant defense against pathogens. There have been many reports on the role of phytohormones in pathogen-induced cell death, but jasmonic acid (JA) has not been implicated as a regulator of the response. Here, /investigators/ report the function of NbHB1, Nicotiana benthamiana homeobox1, in pathogen-induced cell death in connection with JA signaling. Involvement of NbHB1 in cell death was analyzed by gain- and loss-of-function studies using Agrobacterium-mediated transient overexpression and virus-induced gene silencing, respectively. Expression of NbHB1 following pathogen inoculations and various treatments was monitored by reverse transcription polymerase chain reaction. Transcript levels of NbHB1 were upregulated by infection with virulent and avirulent bacterial pathogens. Ectopic expression of NbHB1 accelerated cell death following treatment with darkness, methyl jasmonate, or pathogen inoculation. Conversely, when NbHB1 was silenced, pathogen-induced cell death was delayed. NbHB1-induced cell death was also delayed by silencing of NbCOI1, indicating a requirement for JA-mediated signaling. Overexpression of the domain-deleted proteins of NbHB1 revealed that the homeodomain, leucine zipper, and part of the variable N-terminal region were necessary for NbHB1 functionality. These results strongly suggest the role of NbHB1 in pathogen-induced plant cell death via the JA-mediated signaling pathway.|In this study, /the authors/ employed high throughput Illumina sequencing to identify miRNAs from Taxus chinensis (T. chinensis) cells to investigate the effect of the taxoid elicitor methyl jasmonate (MJ) on miRNA expression. In a dataset of approximately 6.6 million sequences, a total of 58 miRNAs, belonging to 25 families were identified. A majority of them are conserved between angiosperms and gymnosperms. However, two miRNAs (miR1310 and miR1314) appear gymnosperm-specific, with miR1314 likely to exist as a cluster. MJ treatment significantly affected the expression of specific miRNAs; 14 miRNAs from 7 different families (miR156, miR168, miR169, miR172, miR396, miR480 and mir1310) were down regulated whereas 3 miRNAs from 2 families (miR164 and miR390) were up regulated.|For more Mechanism of Action (Complete) data for Methyl Jasmonate (13 total), please visit the HSDB record page.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Jasmonates are plant stress hormones. These small hydrophobic compounds exhibit anti-cancer activities, in vitro and in vivo, against cancer cells of various histological origins. Moreover, they show a selective activity against transformed cells and affect drug-resistant cells as well. The aim of this study was to evaluate the activity of a powerful jasmonate derivative, that is methyl jasmonate. Methyl jasmonate was applied topically on cancerous and pre-cancerous skin lesions from eight patients. Methyl jasmonate did not cause any meaningful local or systemic side effects. Three patients exhibited positive responses. Two patients had complete recovery and one had a recurrence of the lesion three months post treatment. /It was concluded that/ methyl jasmonate is a potentially promising novel topical treatment for pr/e-/cancerous and cancerous skin lesions...|/ALTERNATIVE and IN VITRO TESTS/ ...The present work deals with the anti-angiogenic effects of methyl jasmonate. Jasmonate derivatives were demonstrated to selectively damage the mitochondria of cancer cells. In vitro, 1-10 mM methyl jasmonate induced the cell death of the human umbilical vein endothelial cells (HUVEC)... while umolar concentrations were ineffective...

3-oxo-2-(2-pentenyl)cyclopentaneacetic acid methyl ester

Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-: ACTIVE|Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-rel-: INACTIVE|Cyclopentaneacetic acid, 3-oxo-2-(2-penten-1-yl)-, methyl ester: ACTIVE|Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2S)-rel-: INACTIVE|The main volatile component of jasmin oil is benzyl acetate. However, minor components such as indole, cis-jasmone, and methyl jasmonate contribute strongly to the typical jasmin fragrance.|Methyl jasmonate is a potentially promising novel topical treatment for pr/e-/cancerous and cancerous skin lesions...

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