(Z)-jasmone

cis-jasmone

CAS: 488-10-8 C11 H16 O MW: 164.24772000 floral woody

Identification

Name(Z)-jasmone
IUPAC3-methyl-2-[(Z)-pent-2-enyl]cyclopent-2-en-1-one
CAS Number488-10-8
EINECS207-668-4
FDA UNIIRC4W0G9YUK
Molecular FormulaC11 H16 O
Molecular Weight164.24772000
MDL NumberMFCD00001402
Nikkaji NumberJ2.598D
Beilstein1907713
CoE Number11786

Regulatory

JECFA Food Flavoring1114 3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one
DG SANTE Food Flavourings07.094 3-methyl-2-(pent-2(cis)-enyl)cyclopent-2-en-1-one
FEMA Number3196
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)488-10-8 ; JASMONE, CIS-
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance colorless to pale yellow clear oily liquid (est)
Assay 98.00 to 100.00 sum of isomers
Food Chemicals Codex Listed No
Specific Gravity 0.94200 to 0.94800 @ 25.00 °C.
Pounds per Gallon - (est). 7.838 to 7.888
Refractive Index 1.49500 to 1.50100 @ 20.00 °C.
Boiling Point 134.00 to 135.00 °C. @ 12.00 mm Hg, 257.00 to 258.00 °C. @ 755.00 mm Hg
Vapor Pressure 0.010000 mmHg @ 25.00 °C. (est)
Vapor Density >1 ( Air = 1 )
Flash Point 225.00 °F. TCC ( 107.22 °C. )
logP (o/w) 2.905 (est)
Soluble in alcohol
Insoluble in water
Stability alcoholic fine fragrance, good

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium ,
Substantivity 68 hour(s) at 100.00 %
Odor Description
at 10.00 % in dipropylene glycol.
Woody, herbal and floral, with a citrus nuance
A very diffusive jasmine, celery seed note, with a hint of black tea
Floral, Green, Jasmine, Warm
Floral, Jasmine, Spicy, Fruity
very natural floral, fruity; real character of jasmin flowers
Woody, floral-jasmine, herbal, spicy, celery
A very diffusive jasmine, celery seed note, with a hint of black tea
very diffusive, natural jasmine-tuberose note with a slightly spicy, celery and woody undertone
Odor sample from Takasago International Corp
Taste Description
at 25.00 ppm.
Lactonic, pleasant fuzzy peach, apricot notes
woody bitter tea citrus floral
woody, bitter, tea, with a citrus and floral (jasmin-like) nuance
Lactonic, pleasant fuzzy peach, apricot notes
Lactonic, pleasant fuzzy peach, apricot notes

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Human Experience8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicityoral-rat LD50 5000 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for (Z)-jasmone usage levels up to3.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)13.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)7.20 (μg/capita/day)
Structure ClassII
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

ACS International GmbH

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Potential Uses

FR apricot FR bergamot FR celery FR citrus FR floral freshener FR fruit FR herbal FR honey FR jasmin FR jonquil FR maple FR mint FR neroli FR orange blossom FR peach FR peppermint FR raspberry FR spearmint FL tea FR tobacco FL tomato FR tuberose FR woody

Natural Occurrence

artemisia gypsacea krasch. oil iran @ 0.70% Data bergamot oil @ trace% Data bergamot peel champaca concrete @ 0.05% Data fig leaf horsemint shoot jasmin PMC jasmin absolute concrete egypt @ 2.23% Data jasmin absolute concrete india @ 7.90-9.45% Data jasmin absolute concrete italy @ 2.93% Data jasmin sambac absolute egypt @ 0.45% Data jonquil lime oil CO2 extract mexico @ trace% Data mandarin neroli PMC neroli oil CO2 extract @ 0.15% Data orange osmanthus absolute @ 0.02% Data peppermint peppermint oil peppermint oil mongolia @ 0.04% Data spearmint leaf spearmint oil tea leaf tea leaf oil water mint shoot yarrow oil @ 1.90% Data yarrow oil greece @ 0.80% Data

Synonyms

2- cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- 2- cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- 2- cyclopenten-1-one, 3-methyl-2-[(2Z)-2-penten-1-yl]- 2- cyclopenten-1-one, 3-methyl-2-[(2Z)-2-pentenyl]- (Z)- jasmone cis- jasmone cis jasmone cis- jasmone china jasmone cis 3- methyl-((Z)-2-penten-1-yl)-2-cyclopenten-1-one 3- methyl-(cis-2-penten-1-yl)-2-cyclopenten-1-one 3- methyl-2-(2-cis-pentenyl)-2-cyclopenten-1-one (Z)-3- methyl-2-(2-pentenyl)-2-cyclopenten-1-one 3- methyl-2-(2-pentenyl)-2-cyclopenten-1-one cis-3- methyl-2-(2-pentenyl)-2-cyclopenten-1-one 3- methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one 3- methyl-2-(cis-2-pentenyl)-2-cyclopenten-1-one 3- methyl-2-(pent-2(cis)-enyl)cyclopent-2-en-1-one 3- methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one 3- methyl-2-[(Z)-pent-2-enyl]cyclopent-2-en-1-one US Patents: 3,941,828 - Process for the preparation of cyclic ketones PubMed: Attraction of the orange mint moth and false celery leaftier moth (Lepidoptera: Crambidae) to floral chemical lures. US Patents: 3,981,920 - Method for preparing cyclopentenone derivatives PubMed: Behavioural responses of Frankliniella occidentalis Pergande larvae to methyl jasmonate and cis-jasmone. PubMed: Characterisation of odorant compounds and their biochemical formation in green tea with a low temperature storage process. PubMed: Priming of Production in Maize of Volatile Organic Defence Compounds by the Natural Plant Activator cis-Jasmone. PubMed: Synergistic manipulations of plant and insect defences. PubMed: Synthetic cis-jasmone exposure induces wheat and barley volatiles that repel the pest cereal leaf beetle, Oulema melanopus L. PubMed: Evidence for behavioral attractiveness of methoxylated aromatics in a dynastid scarab beetle-pollinated araceae. PubMed: Activation of defence in sweet pepper, Capsicum annum, by cis-jasmone, and its impact on aphid and aphid parasitoid behaviour. PubMed: Aphid antixenosis in cotton is activated by the natural plant defence elicitor cis-jasmone. PubMed: Fragrance material review on cis-jasmone. PubMed: Liquid CO2 extraction of Jasminum grandiflorum and comparison with conventional processes. PubMed: Predication of Japanese green tea (Sen-cha) ranking by volatile profiling using gas chromatography mass spectrometry and multivariate analysis. PubMed: Emerging roles in plant defense for cis-jasmone-induced cytochrome P450 CYP81D11. PubMed: The transcriptome of cis-jasmone-induced resistance in Arabidopsis thaliana and its role in indirect defence. PubMed: Searching for monooxygenases and hydrolases in bacteria from an extreme environment. PubMed: Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit? PubMed: Attraction of New Zealand flower thrips, Thrips obscuratus, to cis-jasmone, a volatile identified from Japanese honeysuckle flowers. PubMed: Highly selective tuning of a silkworm olfactory receptor to a key mulberry leaf volatile. PubMed: Volatile composition of Catharanthus roseus (L.) G. Don using solid-phase microextraction and gas chromatography/mass spectrometry. PubMed: Delayed cytotoxic effects of methyl jasmonate and cis-jasmone induced apoptosis in prostate cancer cells. PubMed: Methyl jasmonate decreases membrane fluidity and induces apoptosis through tumor necrosis factor receptor 1 in breast cancer cells. PubMed: Natural jasmonates of different structures suppress the growth of human neuroblastoma cell line SH-SY5Y and its mechanisms. PubMed: cis-Jasmone induces Arabidopsis genes that affect the chemical ecology of multitrophic interactions with aphids and their parasitoids. PubMed: Iso-OPDA: an early precursor of cis-jasmone in plants? PubMed: Developments in aspects of ecological phytochemistry: the role of cis-jasmone in inducible defence systems in plants. PubMed: [Effects of different elicitors on olfactory response and oviposition selection of Dendrolimus superans (Butler)]. PubMed: cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum. PubMed: 4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments. PubMed: Treating hop plants with (Z)-jasmone increases colonization by Phorodon humuli (Hemiptera: Aphididae) spring migrants. PubMed: Jasmonates induce apoptosis and cell cycle arrest in non-small cell lung cancer lines. PubMed: Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes. PubMed: Comparison of glass vessels and plastic bags for enclosing living plant parts for headspace analysis. PubMed: Microwave assisted synthesis of fragrant jasmone heterocyclic analogues. PubMed: Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects. PubMed: Ti-crossed-Claisen condensation between carboxylic esters and acid chlorides or acids: a highly selective and general method for the preparation of various beta-keto esters. PubMed: Fragrances in oolong tea that enhance the response of GABAA receptors. PubMed: Methyl jasmonate and cis-jasmone do not dispose of the herbivore-induced jasmonate burst in Nicotiana attenuata. PubMed: cis-Jasmone treatment induces resistance in wheat plants against the grain aphid, Sitobion avenae (Fabricius) (Homoptera: Aphididae). PubMed: Manipulation of parasitoids for aphid pest management: progress and prospects. PubMed: Fatty acid-derived signals in plants. PubMed: New roles for cis-jasmone as an insect semiochemical and in plant defense. PubMed: Effects of volatile compounds on consumption of alfalfa pellets by sheep. PubMed: Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures.