(Z)-citral
neral
Identification
| Name | (Z)-citral |
| IUPAC | (2Z)-3,7-dimethylocta-2,6-dienal |
| CAS Number | 106-26-3 |
| EINECS | 203-379-2 |
| FDA UNII | 8M466BQL1X |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| MDL Number | MFCD03424818 |
| Nikkaji Number | J3.242E |
| CoE Number | 109 |
Regulatory
| DG SANTE Food Flavourings | 05.170 neral |
Physical Properties
| Appearance | pale yellow to yellow clear liquid (est) |
| Assay | 88.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.88100 to 0.89100 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.331 to 7.414 |
| Refractive Index | 1.47800 to 1.49000 @ 20.00 °C. |
| Boiling Point | 228.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.071000 mmHg @ 25.00 °C. |
| Flash Point | 215.00 °F. TCC ( 101.67 °C. ) |
| logP (o/w) | 3.170 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description | at 100.00 %. |
| Odor sample from | CA Aromatics Company Inc. |
| Taste Description | lemon |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| IFRA Critical Effect | Sensitization |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 950.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 69000 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 22.29000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | - |
| Edible ices, including sherbet and sorbet (03.0) | 173.78000 |
| Processed fruit (04.1) | - |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 950.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | - |
| Bakery wares (07.0) | 132.82000 |
| Meat and meat products, including poultry and game (08.0) | 1.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | - |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 10.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 17.33000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 3.00000 |
| Ready-to-eat savouries (15.0) | - |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | - |
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Potential Uses
Natural Occurrence
Synonyms
(Z)-
citral
cis-
citral
(Z)-3,7-
dimethyl octa-2,6-dienal
(Z)-3,7-
dimethyl-2,6-octadienal
cis-3,7-
dimethyl-2,6-octadienal
(2Z)-3,7-
dimethylocta-2,6-dienal
(Z)-
neral
neral refined 94/95% (natural)
neral standard 88% (natural)
neral, refined 60 - 63%
PubMed:
Chemical composition, antioxidant, antimicrobial and cytotoxic activities of Tagetes minuta and Ocimum basilicum essential oils.
PubMed:
HPLC-DAD for the determination of three different classes of antifungals: method characterization, statistical approach, and application to a permeation study.
PubMed:
Essential oils with insecticidal activity against larvae of Aedes aegypti (Diptera: Culicidae).
PubMed:
Antimicrobial constituents and synergism effect of the essential oils from Cymbopogon citratus and Alpinia galanga.
PubMed:
Comparative chemical study and cytotoxic activity of Uvariodendron angustifolium essential oils from Benin.
PubMed:
Suppression of allergic and inflammatory responses by essential oils derived from herbal plants and citrus fruits.
PubMed:
Essential oil from lemon peels inhibit key enzymes linked to neurodegenerative conditions and pro-oxidant induced lipid peroxidation.
PubMed:
Assessment of Cymbopogon citratus (DC.) Stapf Essential Oil as Herbal Preservatives Based on Antifungal, Antiaflatoxin, and Antiochratoxin Activities and In Vivo Efficacy during Storage.
PubMed:
[Compartmentalization of neral non-synaptic plasticity at subcellular level].
PubMed:
The use of bone cement in difficult distal radius fractures.
PubMed:
Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles).
PubMed:
Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin.
PubMed:
Engineering Escherichia coli for selective geraniol production with minimized endogenous dehydrogenation.
PubMed:
Silicone arthroplasty for nonrheumatic metacarpophalangeal joint arthritis.
PubMed:
Chemical composition of the essential oils of variegated pink-fleshed lemon (Citrus x limon L. Burm. f.) and their anti-inflammatory and antimicrobial activities.
PubMed:
Antispasmodic effects and composition of the essential oils from two South American chemotypes of Lippia alba.
PubMed:
Bioefficacy of acyclic monoterpenes and their saturated derivatives against the West Nile vector Culex pipiens.
PubMed:
Effects of drying methods on qualitative and quantitative properties of essential oil of two basil landraces.
PubMed:
Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits.
PubMed:
Behavioural and electroantennogram responses of the stable fly (Stomoxys calcitrans L.) to plant essential oils and their mixtures with attractants.
PubMed:
Chemical composition and in vitro biological activities of the essential oil of Vepris macrophylla (BAKER) I.VERD. endemic to Madagascar.
PubMed:
Vasodilator activity of the essential oil from aerial parts of Pectis brevipedunculata and its main constituent citral in rat aorta.
PubMed:
Terpenoids from Zingiber officinale (Ginger) induce apoptosis in endometrial cancer cells through the activation of p53.
PubMed:
Essential oils and their compositions as spatial repellents for pestiferous social wasps.
PubMed:
Phytochemical composition of Cymbopogon citratus and Eucalyptus citriodora essential oils and their anti-inflammatory and analgesic properties on Wistar rats.
PubMed:
[Genetic counselling in male carriers of BRCA1 and BRCA2 gene mutations].
PubMed:
Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species.
PubMed:
Evaluation of bioefficacy of three Citrus essential oils against the dengue vector Aedes albopictus (Diptera: Culicidae) in correlation to their components enantiomeric distribution.
PubMed:
Functional characterization of SlscADH1, a fruit-ripening-associated short-chain alcohol dehydrogenase of tomato.
PubMed:
Chemical composition of essential oils of Litsea cubeba harvested from its distribution areas in China.
PubMed:
Contact allergy to air-exposed geraniol: clinical observations and report of 14 cases.
PubMed:
Timing of male sex pheromone biosynthesis in a butterfly - different dynamics under direct or diapause development.
PubMed:
Virtual screening and in vitro assay of potential drug like inhibitors from spices against Glutathione-S-Transferase of Meloidogyne incognita.
PubMed:
Development of microemulsion of a potent anti-tyrosinase essential oil of an edible plant.
PubMed:
Antityrosinase and antioxidant activities of essential oils of edible Thai plants.
PubMed:
Enhancement of the antibiotic activity of erythromycin by volatile compounds of Lippia alba (Mill.) N.E. Brown against Staphylococcus aureus.
PubMed:
A dual catalyst system provides the shortest pathway for L-menthol synthesis.
PubMed:
Determining the disinfection of textiles in compressed carbon dioxide using various indicator microbes.
PubMed:
Encapsulation of citral isomers in extracted lemongrass oil with cyclodextrins: molecular modeling and physicochemical characterizations.
PubMed:
Chemical composition and vasorelaxant effect induced by the essential oil of Lippia alba (Mill.) N.E. Brown. (Verbenaceae) in rat mesenteric artery.
PubMed:
Multidimensional enantio gas chromtography/mass spectrometry and gas chromatography-combustion-isotopic ratio mass spectrometry for the authenticity assessment of lime essential oils (C. aurantifolia Swingle and C. latifolia Tanaka).
PubMed:
Chemical constituents and their bioactivities of "Tongling White Ginger" (Zingiber officinale).
PubMed:
Chemical characterization of Lippia alba essential oil: an alternative to control green molds.
PubMed:
Anti-quorum sensing activity of essential oils from Colombian plants.
PubMed:
Chemical composition and antigenotoxic properties of Lippia alba essential oils.
PubMed:
Chemical composition analysis of the essential oil of Melissa officinalis L. from Kurdistan, Iran by HS/SPME method and calculation of the biophysicochemical coefficients of the components.
PubMed:
Chemical composition and antimicrobial activity of Cymbopogon citratus and Cymbopogon giganteus essential oils alone and in combination.
PubMed:
Composition of a monoterpenoid-rich essential oil from the rhizome of Zingiber officinale from north western Himalayas.
PubMed:
Discrimination of Oribotritia species by oil gland chemistry (Acari, Oribatida).
PubMed:
Microparticles containing lemongrass volatile oil: preparation, characterization and thermal stability.
PubMed:
Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil.
PubMed:
Synergistic antimicrobial activity of galangal (Alpinia galanga), rosemary (Rosmarinus officinalis) and lemon iron bark (Eucalyptus staigerana) extracts.
PubMed:
Essential oil polymorphism of wild growing Hungarian thyme (Thymus pannonicus) populations in the Carpathian Basin.
PubMed:
Liquid and vapour-phase antifungal activities of selected essential oils against Candida albicans: microscopic observations and chemical characterization of Cymbopogon citratus.
PubMed:
Multiple neural tube defects in the same patient with no neurological deficit.
PubMed:
The effects of high hydrostatic pressure treatment on the flavor and color of grated ginger.
PubMed:
Chemical composition and antiprotozoal activities of Colombian Lippia spp essential oils and their major components.
PubMed:
Essential-oil composition, antileishmanial, and toxicity study of Artemisia abyssinica and Satureja punctata ssp. punctata from Ethiopia.
PubMed:
Sexual abuse prevention: a training program for developmental disabilities service providers.
PubMed:
Volatile organic components of fresh leaves as indicators of indigenous and cultivated citrus species in Taiwan.
PubMed:
Chemotaxonomic investigations of peel and petitgrain essential oils from 17 citron cultivars.
PubMed:
Bioactivity against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) of Cymbopogon citratus and Eucalyptus citriodora essential oils grown in Colombia.
PubMed:
Nematicidal activity of essential oils and volatiles derived from Portuguese aromatic flora against the pinewood nematode, Bursaphelenchus xylophilus.
PubMed:
Chemical composition and antibacterial activity of essential oils from different parts of Litsea cubeba.
PubMed:
Quantitative determination of some volatile suspected allergens in cosmetic creams spread on skin by direct contact sorptive tape extraction-gas chromatography-mass spectrometry.
PubMed:
Chemical composition of Eucalyptus spp. essential oils and their insecticidal effects on Lutzomyia longipalpis.
PubMed:
Composition and antioxidant properties of the essential oil of the endemic Cape Verdean Satureja forbesii.
PubMed:
Efficacy of Lippia alba (Mill.) N.E. Brown essential oil and its monoterpene aldehyde constituents against fungi isolated from some edible legume seeds and aflatoxin B1 production.
PubMed:
Lemongrass effects on IL-1beta and IL-6 production by macrophages.
PubMed:
Essential oil of Lindera neesiana fruit: chemical analysis and its potential use in topical applications.
PubMed:
Repellent activity of alligator pepper, Aframomum melegueta, and ginger, Zingiber officinale, against the maize weevil, Sitophilus zeamais.
PubMed:
Non-cognitive variables and residency choice.
PubMed:
Site-saturation mutagenesis of tryptophan 116 of Saccharomyces pastorianus old yellow enzyme uncovers stereocomplementary variants.
PubMed:
Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
PubMed:
Male-produced aggregation pheromone blend in Platypus koryoensis.
PubMed:
Menthol and geraniol biotransformation and glycosylation capacity of Levisticum officinale hairy roots.
PubMed:
Processing and storage effects on orange juice aroma: a review.
PubMed:
Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens.
PubMed:
Evaluation of the chemical composition of Brazilian commercial Cymbopogon citratus (D.C.) stapf samples.
PubMed:
Chemical composition and in vitro antimicrobial activity of essential oil of Melissa officinalis L. from Romania.
PubMed:
Evaluation of in vitro antimicrobial activity of Thai basil oils and their micro-emulsion formulas against Propionibacterium acnes.
PubMed:
Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons.
PubMed:
Solid-phase microextraction for determining twelve orange flavour compounds in a model beverage emulsion.
PubMed:
Geraniol dehydrogenase, the key enzyme in biosynthesis of the alarm pheromone, from the astigmatid mite Carpoglyphus lactis (Acari: Carpoglyphidae).
PubMed:
A male-produced aggregation pheromone blend consisting of alkanediols, terpenoids, and an aromatic alcohol from the cerambycid beetle Megacyllene caryae.
PubMed:
Expression of two old yellow enzyme homologues from Gluconobacter oxydans and identification of their citral hydrogenation abilities.
PubMed:
Effect of pulp reduction and pasteurization on the release of aroma compounds in industrial orange juice.
PubMed:
Identification of the genotype from the content and composition of the essential oil of lemon verbena (Aloysia citriodora Palau).
PubMed:
Nematicidal Activity of Plant Essential Oils and Components From Ajowan (Trachyspermum ammi), Allspice (Pimenta dioica) and Litsea (Litsea cubeba) Essential Oils Against Pine Wood Nematode (Bursaphelenchus Xylophilus).
PubMed:
Nematicidal and larvicidal activities of the essential oils from aerial parts of Pectis oligocephala and Pectis apodocephala Baker.
PubMed:
Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization.
PubMed:
Chemical composition and antifungal activity of the essential oils of three species of Artemisia on some soil-borne phytopathogens.
PubMed:
The antimicrobial activity of essential oil from Dracocephalum foetidum against pathogenic microorganisms.
PubMed:
Male sex pheromone release and female mate choice in a butterfly.
PubMed:
Antimicrobial activity of some essential oils against microorganisms deteriorating fruit juices.
PubMed:
Authenticity control of essential oils containing citronellal and citral by chiral and stable-isotope gas-chromatographic analysis.
PubMed:
Chemical alarm and defence in the oribatid mite Collohmannia gigantea (Acari: Oribatida).
PubMed:
Extended surgical resection for xanthogranulomatous cholecystitis mimicking advanced gallbladder carcinoma: A case report and review of literature.
PubMed:
Essential oil composition of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe) grown in Australia.
PubMed:
Analysis of the enzymatic formation of citral in the glands of sweet basil.
PubMed:
[Allelopathic effects of Cymbopogon citratu volatile and its chemical components].
PubMed:
Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production.
PubMed:
Volatile exudates from the oribatid mite, Platynothrus peltifer.
PubMed:
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
PubMed:
Bioactive constituents from Dracocephalum subcapitatum (O. Kuntze) Lipsky.
PubMed:
Ontogenetic changes in the chemistry and morphology of oil glands in Hermannia convexa (Acari: Oribatida).
PubMed:
Metabolism of geraniol in grape berry mesocarp of Vitis vinifera L. cv. Scheurebe: demonstration of stereoselective reduction, E/Z-isomerization, oxidation and glycosylation.
PubMed:
In vivo antimalarial activity of essential oils from Cymbopogon citratus and Ocimum gratissimum on mice infected with Plasmodium berghei.
PubMed:
The effect of solvent interactions on alpha-, beta-, and gamma-cyclodextrin/flavor molecular inclusion complexes.
PubMed:
Identification and biosynthesis of an aggregation pheromone of the storage mite Chortoglyphus arcuatus.
PubMed:
Two new monoterpene glycosides and trypanocidal terpenoids from Dracocephalum kotschyi.
PubMed:
Determination of flavour and off-flavour compounds in orange juice by on-line coupling of a pervaporation unit to gas chromatography-mass spectrometry.
PubMed:
Headspace solid-phase microextraction for characterization of fragrances of lemon verbena (Aloysia triphylla) by gas chromatography-mass spectrometry.
PubMed:
Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil.
PubMed:
Analysis of anal secretions from phlaeothripine thrips.
PubMed:
Characterization of geraniol synthase from the peltate glands of sweet basil.
PubMed:
Chemical ecology of oribatid mites III. Chemical composition of oil gland exudates from two oribatid mites, Trhypochthoniellus sp. and Trhypochthonius japonicus (Acari: Trhypochthoniidae).
PubMed:
Semiochemicals from the predatory stink bug Eocanthecona furcellata (Wolff): components of metathoracic gland, dorsal abdominal gland, and sternal gland secretions.
PubMed:
Toxicity of Australian essential oil Backhousia citriodora (lemon myrtle). Part 2. Absorption and histopathology following application to human skin.
PubMed:
Analysis of some Italian lemon liquors (limoncello).
PubMed:
Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture.
PubMed:
Activity of essential oils from Mediterranean Lamiaceae species against food spoilage yeasts.
PubMed:
A phase II detoxification enzyme inducer from lemongrass: identification of citral and involvement of electrophilic reaction in the enzyme induction.
PubMed:
[A study on the effect and mechanism of acupuncture suppression of neuronal apoptosis following cerebral ischemia].
PubMed:
Assessment of estrogenic activity in some common essential oil constituents.
PubMed:
Chemistry of the oil gland secretion of Collohmannia gigantea (Acari: Oribatida).
PubMed:
Comparison of extraction methods for marker compounds in the essential oil of lemon grass by GC.
PubMed:
Volatile components of peel and leaf oils of lemon and lime species.
PubMed:
Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety.
PubMed:
Degradation of monoterpenes in orange juice by gamma radiation.
PubMed:
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:
Changes in essential oil during enzyme-assisted ensiling of lemongrass (Cymbopogon citratus Stapf.) and lemon eucalyptus (Eucalyptus citriodora Hook).
PubMed:
Biotransformation of constituents of essential oils by germinating wheat seed.
PubMed:
Amino acid-catalyzed conversion of citral: cis-trans isomerization and its conversion into 6-methyl-5-hepten-2-one and acetaldehyde.
PubMed:
Encapsulation of lemon oil by paste method using beta-cyclodextrin: encapsulation efficiency and profile of oil volatiles.
PubMed:
The main citral-geraniol and carvacrol chemotypes of the essential oil of thymus pulegioides L. growing wild in vilnius district (Lithuania).
PubMed:
Grapefruit gland oil composition is affected by wax application, storage temperature, and storage time.
PubMed:
Mechanism of inhibition of aldehyde dehydrogenase by citral, a retinoid antagonist.
PubMed:
Infraspecific taxonomy and essential oil chemotypes in sweet basil, Ocimum basilicum.
PubMed:
Genetic analysis of essential oil variants in Perilla frutescens.
PubMed:
Prediction of medical student achievement by the utilization of personality characteristics and personal values.
PubMed:
Stress, coping, and well-being among third-year medical students.
PubMed:
Variation with caste of the mandibular gland secretion in the leaf-cutting antAtta sexdens rubropilosa.
PubMed:
The effects of malpractice on Mississippi physicians.
PubMed:
Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols.
PubMed:
The metabolism of 3,7-dimethyl-2,6-octadienal (citral) in rat hepatic mitochondrial and cytosolic fractions. Interactions with aldehyde and alcohol dehydrogenases.
PubMed:
Metabolism of citral, an alpha,beta-unsaturated aldehyde, in male F344 rats.
PubMed:
Robber bees (Lestrimelitta limao) and their host chemical and visual cues in nest defense byTrigona (Tetragonisca) angustula (Apidae: Meliponinae).
PubMed:
Chemistry of mandibular and Dufour's gland secretions of ants in genusMyrmecocystus.
PubMed:
Antibacterial constituents in the essential oil of Cymbopogon citratus (DC.) Stapf.
PubMed:
The Role of 9- and/or 10-oxygenated Derivatives of Geraniol, Geranial, Nerol, and Neral in the Biosynthesis of Loganin and Ajmalicine.
PubMed:
Exocrine secretions of bees V. Terpenoid esters in the Dufour's secretions ofPanurginus bees (Hymenoptera: Andrenidae).
PubMed:
A comparative study of the exocrine products of cleptoparasitic bees (Holcopasites) and their hosts (Calliopsis) (Hymenoptera: Anthophoridae, Andrenidae).
PubMed:
[Chemical composition of the essential oil from melissa].
PubMed:
Biogenesis of monoterpenes : Bioconversion of citral by a cell suspension culture of muscat grapes.
PubMed:
Mandibular glands of maleCentris adani, (Hymenoptera: Anthophoridae) : Their morphology, chemical constituents, and function in scent marking and territorial behavior.
PubMed:
The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers.
PubMed:
An electrophysiological study of the sacral parasympathetic pathway to the colon of the cat.
PubMed:
[Positive experience with paracervical block in minor gynecological surgery].
PubMed:
Skimania.