delta-elemene
(1S,2R)-(-)-2-isopropenyl-1-vinyl-p-menth-3-ene
Identification
| Name | delta-elemene |
| IUPAC | (3S,4R)-4-ethenyl-4-methyl-1-propan-2-yl-3-prop-1-en-2-ylcyclohexene |
| CAS Number | 20307-84-0 |
| FDA UNII | Search |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| CoE Number | 10996 |
Regulatory
| DG SANTE Food Flavourings | 01.039 delta-elemene |
Physical Properties
| Appearance | colorless to yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.85600 to 0.86200 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.123 to 7.173 |
| Refractive Index | 1.48000 to 1.48600 @ 20.00 °C. |
| Boiling Point | 254.00 to 255.00 °C. @ 760.00 mm Hg (est), 107.00 °C. @ 10.00 mm Hg |
| Vapor Pressure | 0.028000 mmHg @ 25.00 °C. (est) |
| Flash Point | 211.00 °F. TCC ( 99.50 °C. ) (est) |
| logP (o/w) | 6.446 (est) |
| Soluble in | water, 0.01368 mg/L @ 25 °C (est) |
Organoleptic Properties
| Odor Description | at 100.00 %. |
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 |
| Recommendation for delta-elemene usage levels up to | 3.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.012 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 7.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 5.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 10.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 4.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 20.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
1,3,6-
elematriene
(3S,4R)-4-
ethenyl-4-methyl-1-propan-2-yl-3-prop-1-en-2-ylcyclohexene
(3R-(E))-4-
ethenyl-4-methyl-3-(1-methyl ethenyl)-1-(1-methyl ethyl) cyclohexene
(3R-trans)-4-
ethenyl-4-methyl-3-(1-methyl ethenyl)-1-(1-methyl ethyl) cyclohexene
(1S,2R)-(-)-2-iso
propenyl-1-vinyl-p-menth-3-ene
(1S,2R)-(-)-2-iso
propenyl-1-vinyl-para-menth-3-ene
PubMed:
Chemical compositions and antimicrobial activity of the essential oils of Hornstedtia havilandii (Zingiberaceae).
PubMed:
Combined analysis of the root bark oil of Cleistopholis glauca by chromatographic and spectroscopic techniques.
PubMed:
Chemical composition of essential oils from the leaves and stem barks of Vietnamese species of Polyalthia harmandiiPolyalthia jucunda and Polyalthia thorelii.
PubMed:
Constituents of essential oils from the leaves, stem barks and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam.
PubMed:
Comparative analysis of the essential oil composition of Murraya paniculata and M. exotica.
PubMed:
Essential oils composition of croton species from the Amazon.
PubMed:
Quantitative Analysis and Discrimination of Steamed and Non-Steamed Rhizomes of Curcuma wenyujin by GC-MS and HPLC.
PubMed:
Chemical composition and antimicrobial activity of three essential oils from Curcuma wenyujin.
PubMed:
Chemical composition and anti-Trypanosoma cruzi activity of essential oils obtained from leaves of Xylopia frutescens and X. laevigata (Annonaceae).
PubMed:
Analysis of Cleistopholis patens leaf and trunk bark oils using combined GC- flame ionisation detection, GC-retention index, GC-MS and (13) C-NMR.
PubMed:
Essential oils from five species of Annonaceae from Vietnam.
PubMed:
Antimicrobial Potential and Chemical Characterization of Serbian Liverwort (Porella arboris-vitae): SEM and TEM Observations.
PubMed:
Antimicrobial activity of selected essential oils against cariogenic bacteria.
PubMed:
Antifungal and antibacterial activity of the essential oil of Chamaecyparis lawsoniana from Spain.
PubMed:
Study on the volatile oil contents of Annona glabra L., Annona squamosa L., Annona muricata L. and Annona reticulata L., from Vietnam.
PubMed:
Chemical composition of the essential oils of Centaurea formanekii and C. orphanidea ssp. thessala, growing wild in Greece.
PubMed:
Chemical composition and biological activities of the essential oils from Duguetia lanceolata St. Hil. barks.
PubMed:
Furanodiene induces endoplasmic reticulum stress and presents antiproliferative activities in lung cancer cells.
PubMed:
Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae--a review.
PubMed:
Differences in the volatile compositions of ginseng species (Panax sp.).
PubMed:
Composition and antioxidant capacity of the essential oil of leaves of Vitex megapotamica (Sprengel) Moldenke.
PubMed:
Natural product studies of U.S. endangered plants: volatile components of Lindera melissifolia (Lauraceae) repel mosquitoes and ticks.
PubMed:
Volatiles from Magnolia grandiflora flowers: comparative analysis by simultaneous distillation-extraction and solid phase microextraction.
PubMed:
The leaf essential oils of five Vietnamese Desmos species (Annonaceae).
PubMed:
Chemical and biological analyses of the essential oils and main constituents of Piper species.
PubMed:
Induction of caspase-3-dependent apoptosis in human leukemia HL-60 cells by δ-elemene.
PubMed:
Fractionation of volatile constituents from curcuma rhizome by preparative gas chromatography.
PubMed:
California Lomatiums, Part X. Comparison of composition of the hydrodistilled oils from two subspecies of Lomatium mohavense.
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
B-cell lymphoma-2 over-expression protects δ-elemene-induced apoptosis in human lung carcinoma mucoepidermoid cells via a nuclear factor kappa B-related pathway.
PubMed:
Lysosomal membrane permeabilization contributes to elemene emulsion-induced apoptosis in A549 cells.
PubMed:
The compositions of volatiles and aroma-active compounds in dried omija fruits (Schisandra chinensis Baillon) according to the cultivation areas.
PubMed:
Insecticidal compounds from the essential oil of Chinese medicinal herb Atractylodes chinensis.
PubMed:
Comparative volatile oil composition of four Ocimum species from northern India.
PubMed:
Chemical composition and antibacterial activity of the essential oil of Drimys granadensis L.f. leaves from Colombia.
PubMed:
Essential oil composition of Vismia macrophylla leaves (Guttiferae).
PubMed:
Caryophyllene oxide-rich essential oils of Lithuanian Artemisia campestris ssp. campestris and their toxicity.
PubMed:
Phytochemical investigation of Verbesina turbacensis Kunth: trypanosome cysteine protease inhibition by (-)-bornyl esters.
PubMed:
Essential oils from two Lantana species with antimycobacterial activity.
PubMed:
Cell apoptosis induced by delta-elemene in colorectal adenocarcinoma cells via a mitochondrial-mediated pathway.
PubMed:
Essential oil composition from two species of Piperaceae family grown in Colombia.
PubMed:
Antiatherogenic activity of Dendropanax morbifera essential oil in rats.
PubMed:
Seasonal variation and bioactivity in the leaf oil of Liriodendron tulipifera growing in Huntsville, Alabama.
PubMed:
GC-MS analysis and antimicrobial activity of essential oil of Stachys cretica subsp. smyrnaea.
PubMed:
Essential oil compositions of three Lantana species from Monteverde, Costa Rica.
PubMed:
Antiulcerogenic and anti-inflammatory activities of the essential oil from Pterodon emarginatus seeds.
PubMed:
Synthesis and in vitro anti-proliferative activity of beta-elemene monosubstituted derivatives in HeLa cells mediated through arrest of cell cycle at the G1 phase.
PubMed:
Chemical constituents and larvicidal property of the essential oil of Blumea mollis (D. Don) Merr. against Culex quinquefasciatus.
PubMed:
Antiectoparasitic activity of the gum resin, gum haggar, from the East African plant, Commiphora holtziana.
PubMed:
Bioactivity and chemical composition of the leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum from Monteverde, Costa Rica.
PubMed:
Volatile components from the roots of Solanum pseudocapsicum.
PubMed:
[Extraction and identification of volatile constituents in the flowers of Aglaia odorata Lour].
PubMed:
The volatile constituents analysis of Eremostachys macrophylla Montbr. & Auch. from Iran.
PubMed:
Effect of delta-elemene on Hela cell lines by apoptosis induction.
PubMed:
Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes.
PubMed:
[Radiosensitization of beta-elemene on VX2 carcinoma transplanted on kidney in rabbits in vivo].
PubMed:
[Analysis of volatile constituents in leaves of three cypress species by gas chromatography/mass spectrometry].
PubMed:
Determination of Teucrium chamaedrys volatiles by using direct thermal desorption-comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry.
PubMed:
Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components.
PubMed:
Headspace solid-phase microextraction-gas chromatography--mass spectrometry analysis of the volatile compounds of Evodia species fruits.
PubMed:
Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry.
PubMed:
Analysis of leaf surface sesquiterpenes in potato varieties.
PubMed:
Herbal drug quality and phytochemical composition of Hypericum perforatum L. affected by ash yellows phytoplasma infection.
PubMed:
Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott.
PubMed:
Isogermacrene A, a proposed intermediate in sesquiterpene biosynthesis.
PubMed:
Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius.
PubMed:
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
PubMed:
Interspecific variation in terpenoid composition of defensive secretions of European Reticulitermes termites.
PubMed:
Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry.
PubMed:
Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.
PubMed:
[Clinical study on treatment of 40 cases of malignant brain tumor by elemene emulsion injection].
PubMed:
Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia.
PubMed:
(+)-Germacrene A biosynthesis . The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
PubMed:
Volatile constituents of Origanum vulgare ssp. viride (syn. O. heracleoticum) from Iran.
PubMed:
[Essential oil components in leaves and stems of Piper bisasperatum (Piperaceae)].
PubMed:
Production of volatile sesquiterpenes by Fusarium sambucinum strains with different abilities to synthesize trichothecenes.
PubMed:
Germacrene-C, precursor of delta-elemene.