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HCID 636822Erstellt: 27. Oktober 2026

(E)-1,2,4-Trimethoxy-5-prop-1-enylbenzol

ASARONE · α-Asarone · A-ASARONE · alpha-Asarion · Asarin · Asaron · (E)-Asarone · alpha-Asaron

https://huagongshe.com/de/chemical/636822

Molekülstruktur von (E)-1,2,4-Trimethoxy-5-prop-1-enylbenzol

Identifikatoren & physikalische Daten

CAS No.2883-98-9
SummenformelC12H16O3
Durchschnittliche Molmasse208,25 g/mol
Monoisotopische Masse208,10994437 g/mol
SMILESC/C=C/c1cc(OC)c(OC)cc1OC
InChIKeyRKFAZBXYICVSKP-AATRIKPKSA-N
PubChem CID636822
ChEMBLCHEMBL333306
ChEBICHEBI:78309
EC No.220-743-6
DTXSIDDTXSID00871878
Lokaler Name(E)-1,2,4-Trimethoxy-5-prop-1-enylbenzol

Chemische & physikalische Eigenschaften

XLogP3
Polarare Oberfläche (TPSA)27,7
H-Brücken-Donoren0
H-Brücken-Akzeptoren3
Frei drehbare Bindungen4
Schwere Atome15
Formalladung0
Komplexität203
DuftstoffeFragrance substance (cis-and trans-Asarone) -> IFRA amendment 40
PestizidePesticides -> Other Insecticides
LogP (Verteilungskoeffizient)2.44
Color/FormMONOCLINIC NEEDLES FROM WATERNeedles from light petroleum
LöslichkeitYellow to medium brown, moderately viscous liquid with a pleasant, spicy aromatic odor. Acid value: max 4. Ester value: 3-20. Solubility 1 vol in 5 vol of 90% ethanolsolutions may be turbid /cis-asarone/Practically insol in watersol in alcohol, ether, glacial acetic acid, carbon tetrachloride, chloroform, petroleum etherSoluble in chloroform, methanol.
Siedepunkt296 °C @ 760 MM HG296 °C(lit.)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Schmelzpunkt62-63 °CCrystals. MP: 67 °C. Insoluble in watersoluble in alcohol /isomer not specified/62 - 63 °C57-61 °C(lit.)
Dampfdruck0.0015 [mmHg]
BrechungsindexINDEX OF REFRACTION: 1.5683 @ 20 °C/DSADTLER REF NUMBER: 34263 (IR, PRISM)Index of refraction: 1.5719 at 11 °C/D1.5060 (estimate)
Physical DescriptionSolid[HSDB] Fine faintly yellow crystals[MSDSonline]
Other Experimental PropertiesDensity: 0.940-0.980 at 25 °C/25 °C. Index of refraction: 1.5010-1.5160 at 20 °C/D. Specific optical rotation: -5 deg to +35 deg. /cis-asaroneEuropean/Density: 1.060-1.080 at 25 °C/25 °C. Index of refraction: 1.5500-1.55525 at 20 °C/D. Specific optical rotation: -2 deg to +6.5 deg. /cis-asaroneIndian/
Dichte1.1227 (rough estimate)
LagerbedingungenKeep in dark place,Sealed in dry,2-8°C
AggregatzustandSolid
FarbeWhite to Off-White
BRN1910606
InChIInChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+
InChIKeyRKFAZBXYICVSKP-AATRIKPKSA-N
SMILESC1(OC)=CC(/C=C/C)=C(OC)C=C1OC
LogP (Verteilungskoeffizient)3.406 (est)
CAS Datenbank2883-98-9(CAS DataBase Reference)
NIST chemische InformationenAsarone(2883-98-9)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (91.5%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 130 reports by companies from 2 notifications to the ECHA C&L Inventory.
GefahrenübersichtIn high-dose animal studies, beta-asarone caused anemia and injury to the heart and liver[HSDB] May cause irritation[MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (91.5%)
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
WechselwirkungenThe action of asarone and beta-asarone, alone or in combination with either reserpine or chloropromazine, on conditioned avoidance behavior in rats, fighting behavior in mice, and electroshock convulsions in rats was determined. ... Asarone potentiated the action of reserpine and chlorpromazine on conditioned avoidance behavior and fighting behaviorbeta-asarone did not. ... Asarone potentiated the lethal effect of chlorpromazine during electroshock convulsionsbeta-asarone did not. Pretreatment with Acorus oil, asarone, or beta-asarone did not increase the concentration of 5-hydroxytryptamine in rat brain. /Asarones/
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Natural Pollution SourcesFROM ROOT OF ASARUM EUROPAEUM L, ARISTOLOCHIACEAE BY DISTILLATION WITH WATER. ALSO FOUND IN ETHEREAL OILS OF A EUROPAEUM & A ARIFOLIUM L, ARISTOLOCHIACEAE & IN ACORUS CALAMUS L, ARACEAE. ISOLATION: GATTERMANN, EGGERS, BER 32, 289 (1899).
Human Toxicity Excerpts/GENOTOXICITY/ The effect of alpha-asarone, a chemical with hypocholesterolemic properties on Sister Chromatid Exchange (SCE) induction was studied in human lymphocytes in vitro ... A slight but consistent increase in SCE was observed ...
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ beta-Asarone doubled sleeping time with sodium pentobarbital in mice at a dose of 50 mg/kg bw i.p. and doubled the sleeping time with ethanol at a dose of 75 mg/kg. /beta-Asarone//LABORATORY ANIMALS: Acute Exposure/ ... a study was conducted of the biological properties of alpha-asarone (1-propenyl-2,4,5- methoxybenzol)--etherophenol, isolated by the authors from the roots of Asarum europaeum. It was determined that the LD50 of asarone for mice in enteral administration was 417.6 mg/kg, in intra-abdominal 310 mg/kg .../LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... The drug alpha-asarone (3, 6 and 9 mg/kg bw, ip, for 30 days) ... was administered intraperitoneally 1/2 hr before the animals were exposed to noise-stress (100 dB for 4 hr/day, for 30 days) . ... All the three doses of alpha-asarone had an effectively protective role, by normalizing the increased superoxide dismutase and lipid peroxidation, decreased catalase, glutathione peroxidase, levels of reduced glutathione, Vitamins C and E and protein thiols due to noise exposure. Thus, action of alpha-asarone against noise-stress may be due its antioxidant property .../LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 25 male and 25 female rats were fed diets containing 0, 400, 800, or 2000 ppm (0, 0.04, 0.08, or 0.2%) beta-asarone for two years. A positive control group of the same size received 2500 ppm (0.25%) Jammu oil of calamus (JOC/approx. 75% beta-asarone/). None of the group receiving 2000 ppm (0.2%) beta-asarone or 2500 ppm (0.25%) JOC survived more than 84 weeksmortality was also increased on the 800 ppm (0.08%) dose. Median survival time in the females was less than in the males in these groups. The gross pathological changes observed were serous fluid in the abdominal and pleural cavities, liver and kidney changes, and tumourous masses in the intestinal tract. The tumors were identified as leiomyosarcomas of the small intestine and were found in one rat on 400 ppm (0.04%), six on 800 ppm (0.08%), nine on 2000 ppm (0.2%) and one on 2500 ppm (0.25%) JOC. All the test rats with leiomyosarcomas were males. The earliest tumor was observed in a rat 52 weeks old on the 2000 ppm (0.2%) dose. Two leiomyosarcomas were also noted in control females but the location differed from that of the tumors in the treated animals. Atrophy of cardiac muscle cells occurred in controls and all test groups but was most prominent in the 2000 ppm (0.2%) beta-asarone and 2500 ppm (0.25%) JOC groups. Cardiac fibrosis generally paralleled the incidence of cardiac atrophy. Fatty degeneration and fatty infiltration were also in the heart more severe in the treated groups. Thrombosis within the chambers of the heart was observed in the 800 and 2000 ppm (0.08 and 0.27%) beta-asarone and 2500 ppm (0.25%) JOC treated groups. Passive hyperemia of the lung, kidneys and liver was more prominent in the test than control animals indicating faulty cardiac function in the test animals. Incidence of hepatic angiectasis and hepatic coagulative necrosis also tended to increase with increasing beta-asarone dose. Both sexes on 800 and 2000 ppm (0.08 and 0.2%) beta-asarone and 2500 ppm (0.25%) JOC had slightly depressed body weights throughout the studythe males on 400 ppm (0.04%) ß-asarone also had depressed body weights at termination but the number of survivors was small. Hemoglobin, hematocrit, and red and white cell counts were normal except that when the test animals became sick they became anemic with lowered hemoglobin, hematocrit, and red cell count. /beta-Asarone/For more Non-Human Toxicity Excerpts (Complete) data for TRANS-ASARONE (14 total), please visit the HSDB record page.
Non-Human Toxicity ValuesLD50 Rat oral 1010 mg/kg bw /beta-Asarone/LD50 Mouse oral 184.2 mg/kg bw /beta-asarone/LD50 Mouse oral 418 mg/kgLD50 Mouse ip 310 mg/kg
Wassergefährdungsklasse (WGK)3
Zollcode29093090
RTECS-Nr.DC2975000
R-Sätze (R)22
Toxizitätbird - wild,LD50,oral,750mg/kg (750mg/kg),Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
GefahrensymboleXn
Sicherheitshinweise (S)22-24/25
Lagerklasse13 - Non Combustible Solids
Gefahrstoffdaten2883-98-9(Hazardous Substances Data)
GefahrenklasseAcute Tox. 4 Oral