HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dihydrocumarin
3,4-DIHYDROCOUMARIN · HYDROCOUMARIN · CHROMAN-2-ONE · 3,4-DIHYDRO-2H-1-BENZOPYRAN-2-ONE · FEMA 2381 · MELILOTIN · 2-Chromanone · BENZODIHYDROPYRONE
Identifikatoren & physikalische Daten
| CAS No. | 119-84-6 |
|---|---|
| Summenformel | C9H8O2 |
| Durchschnittliche Molmasse | 148,16 g/mol |
| Monoisotopische Masse | 148,05242949 g/mol |
| SMILES | O=C1CCc2ccccc2O1 |
| InChIKey | VMUXSMXIQBNMGZ-UHFFFAOYSA-N |
| PubChem CID | 660 |
| ChEMBL | CHEMBL89306 |
| ChEBI | CHEBI:16151 |
| EC No. | 204-354-9 |
| DTXSID | DTXSID2020474 |
| Lokaler Name | Dihydrocumarin |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 165 |
| Geruch | HerbalOdor similar to coumarin at room temp or reminiscent of nitrobenzene at higher temp.Coconut odorHay-like |
| Geschmack | Sweet then bitterBurning |
| Dichte | 1.169 at 64 °F (NTP, 1992) - Denser than waterwill sink1.169 @ 18 °C1.186-1.1921.169 g/mL at 25 °C (lit.) |
| Color/Form | LeafletsWhite to light yellow, oily liquidColorless crystals |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Slightly soluble in ether and carbon tetrachloride1:2.5-3.5 IN 70% ALCOHOLSoluble in chloroform.Soluble in chlorinated solventsIn water, 3,000 mg/l at 37 °CChloroform, Methanol (Sparingly)insoluble |
| Flammpunkt | 266 °F (NTP, 1992)130 °C>230 °F |
| Siedepunkt | 522 °F at 760 mmHg (NTP, 1992)272 °C271.00 to 272.00 °C. @ 760.00 mm Hg272 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 77 °F (NTP, 1992)25 °C24-25 °C (lit.) |
| Dampfdruck | 13.4 mmHg at 77 °F19.5 mmHg at 108 °F27.4 mmHg at 145 °F (NTP, 1992)13.4 [mmHg]13.6kPa at 20℃ |
| Brechungsindex | Index of refraction: 1.5563 @ 20 °C/D1.555-1.559n20/D 1.556(lit.) |
| Physical Description | 3,4-dihydrocoumarin is a white to pale yellow clear oily liquid with a sweet odor. Solidifies around room temperature. (NTP, 1992)White to light yellow liquidColorless solid[HSDB] Low melting solidmp = 24-26 deg C[MSDSonline]colourless to pale yellow liquidcoconut-like aroma |
| FEMA | 2381 | DIHYDROCOUMARIN |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Aggregatzustand | Solid |
| Farbe | Colourless to Off-White |
| Wichte | 1.169 |
| Geruch | at 10.00 % in dipropylene glycol. sweet tonka coumarinic coconut herbal cinnamon balsamic |
| Geruchsart | tonka |
| Biologische Quelle | synthetic |
| JECFA Number | 1171 |
| BRN | 4584 |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCEPERFUMING |
| InChI | 1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2 |
| InChIKey | VMUXSMXIQBNMGZ-UHFFFAOYSA-N |
| SMILES | O=C1CCc2ccccc2O1 |
| LogP (Verteilungskoeffizient) | 1.82 at 25℃ |
| CAS Datenbank | 119-84-6(CAS DataBase Reference) |
| NIST chemische Informationen | 2H-1-Benzopyran-2-one, 3,4-dihydro-(119-84-6) |
| EPA chemische Informationen | 3,4-Dihydrocoumarin (119-84-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]H317 (97.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1702 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 2H-1-Benzopyran-2-one, 3,4-dihydro-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 05-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/22066Dihydrocoumarin: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Coumarins: Human health tier II assessment |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes and mucous membranes.ACUTE/CHRONIC HAZARDS: This compound causes skin, eye and mucous membrane irritation. (NTP, 1992) |
| Gefahrenübersicht | Emergency treatment: CoumarinAfter an ingestion of 4 grams of coumarin, a patient developed muscle paralysis but no cardiovascular effectsHas liver toxicity in rats, but humans are relatively resistantNot active as an anti-coagulant[HSDB] Safe when used as a flavoring agent in food[JECFA] A tumorigen and irritantCaused somnolence in lethal-dose feeding studies of rats[RTECS] A skin, eye, and mucous membrane irritant[CAMEO] An irritant[MSDSonline] See Coumarin. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | Opdyke DLJ Food Cosmet Toxicol 12 (4): 521 (1974). Review with 9 references on irritation, sensitization and toxicity of dihydrocoumarin.DHHS/NTPToxicology & Carcinogenesis Studies of 3,4-Dihydrocoumarin in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 423 (1993) NIH Publication No. 93-3154 |
| Reactivity Profile | 3,4-DIHYDROCOUMARIN is a lactone (behaves as an ester). Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This chemical may hydrolyze under alkaline or acidic conditions. (NTP, 1992) |
| Air and Water Reactions | Solutions of the chemical in water are stable for less than two hours. Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (> 99.9%)Skin Sens. 1 (97.4%)Acute toxicity - category 4Skin sensitisation - category 1 |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material at ambient temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992) |
| Entsorgungsverfahren | SRP: At the time of review, 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. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wechselwirkungen | The following drugs ... may increase ... response to coumarin or indandione derivatives: alcohol (acute intoxication), allopurinol, aminosalicylic acid, amiodarone, anabolic steroids, chloral hydrate, chloramphenicol, cimetidine, clofibrate, co-trimoxazole, danazol, dextrothyroxine sodium, diazoxide, diflunisal, disulfiram, erythromycin, ethacrynic acid, fenoprofen calcium, glucagon, ibuprofen, indomethacin, influenza virus vaccine, isoniazid, meclofenamate, mefenamic acid, methylthiouracil, metronidazole, miconazole, nalidixic acid, neomycin (oral), pentoxifylline, phenylbutazone, propoxyphene, propylthiouracil, quinidine, quinine, salicylates, streptokinase, sulfinpyrazone, sulfonamides, sulindac, tetracyclines, thiazides, thyroid drugs, tricyclic antidepressants, urokinase, vitamin E. /Coumarin & indandione derivatives/The following drugs ... may ... decrease ... response to coumarin or indandione derivatives: alcohol (chronic alcoholism), barbiturates, carbamazepine, corticosteroids, corticotropin, ethchlorvynol, glutethimide, griseofulvin, mercaptopurine, methaqualone, oral contraceptives containing estrogen, rifampin, spironolactone, vitamin K. /Coumarin & indandione derivatives/ |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxinOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=119-84-6] |
| Natural Pollution Sources | Reported found in Melilotus officinalis (Phipson, Chem News, 32, 25, 1875), from which it may be extracted by water distillation. |
| Carcinogen Classification | 3,4-DihydrocoumarinTR-423: Toxicology and Carcinogenesis Studies of 3,4-Dihydrocoumarin (CASRN 119-84-6) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1993 )06/23/92Some EvidenceNo Evidence |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ ...Decreased /nasal/ P450 levels were observed /in rats/ at 24 hr, 48 hr, and 7 days following /a single ip injection of 50 mg/kg coumarin/, with minimal levels seen at 48 hr. The decr in P450 levels was accompanied by necrosis, cell loss, and basal cell metaplasia in the olfactory mucosa. Ip injection of 7-hydroxycoumarin or 3,4-dihydrocoumarin at 50 mg/kg did not result in depletion of nasal P450... ./LABORATORY ANIMALS: Acute Exposure/ ...3,4-Dihydrocoumarin (DHC), which is not a mouse lung carcinogen, did not cause Clara cell injury when dosed to mice at 800 mg/kg. This finding suggests, because DHC lacks a 3,4-double bond, that bioactivation of coumarin to a 3,4-epoxide intermediate may contribute to mouse lung Clara cell toxicity. .../LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ...The effects of ...admin over a 13 wk period of coumarin and three coumarin derivatives, dihydrocoumarin (DHC), 3,4-dimethylcoumarin (3,4-DMC), and 6-methylcoumarin (6-MC) were compared. Coumarin was administered at dietary levels of 0.5 and 0.75% and 3,4-DMC was administered at equimolar dietary levels of 0.6 and 0.9%, respectively. DHC and 6-MC were administered at dietary levels of 0.76 and 0.82%, respectively, equimolar to the 0.75% coumarin dietary level. ...Rats fed equimolar doses of DHC, 3,4-DMC, or 6-MC showed increased relative liver weight and hepatic gamma-glutamyltransferase activityhowever, these compounds did not produce any marked hepatotoxic effects. .../LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ...Under the conditions of these 2 yr gavage studies, there was some evidence of carcinogenic activity of 3,4-dihydrocoumarin in male F344/N rats based on increased incidences of renal tubule adenomas and focal hyperplasia. The transitional cell carcinomas in two 600 mg/kg males may also have been chemical related. There was no evidence of carcinogenic activity of 3,4-dihydrocoumarin in female F344/N rats receiving 150, 300, or 600 mg/kg. There was no evidence of carcinogenic activity of 3,4-dihydrocoumarin in male B6C3FI mice receiving 200, 400, or 800 mg/kg. There was some evidence of carcinogenic activity in female B6C3F1 mice based on increased incidences of hepatocellular adenoma and hepatocellular adenoma or carcinoma (combined)./GENOTOXICITY/ Results from two Salmonella typhimurium gene mutation tests with or without S9 were negative. |
| Populations at Special Risk | SRP: Persons with bleeding disorders or who are taking anticoagulants should be protected from exposure. |
| National Toxicology Program Studies | Toxicity and carcinogenicity studies were conducted by administering 3,4-dihydrocoumarin (99% pure) in corn oil by gavage to groups of male and female F344/N rats and B6C3F1 mice for ... 2 yr. ... 2 YEAR STUDY IN MICE: Groups of 70 male and 70 female mice received 3,4-dihydrocoumarin in corn oil by gavage at doses of 0, 200, 400 or 800 mg/kg body weight. ... 2 YEAR STUDY IN RATS: Groups of 60 male and female rats received 3,4-dihydrocoumarin in corn oil by gavage at doses of 0, 150, 300, or 600 mg/kg body weight. ... CONCLUSIONS: Under the conditions of these 2 yr gavage studies, there was some evidence of carcinogenic activity of 3,4-dihydrocoumarin in male F344/N rats based on increased incidences of renal tubule adenomas and focal hyperplasia. The transitional cell carcinomas in two 600 mg/kg males may also have been chemical related. There was no evidence of carcinogenic activity of 3,4-dihydrocoumarin in female F344/N rats receiving 150, 300, or 600 mg/kg. There was no evidence of carcinogenic activity of 3,4-dihydrocoumarin in male B6C3FI mice receiving 200, 400, or 800 mg/kg. There was some evidence of carcinogenic activity in female B6C3F1 mice based on increased incidences of hepatocellular adenoma and hepatocellular adenoma or carcinoma (combined). |
| Non-Human Toxicity Values | LD50 Rat oral 1460 mg/kgLD50 Mouse ip 200 mg/kgLD50 Guinea pig oral 1760 mg/kg |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29322980 |
| RTECS-Nr. | MW5775000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | The acute oral LD50 value in rats was reported as 1.65 g/kg (1.47-1.83 g/ kg) (Moreno, 1972a). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Moreno, 1972b). |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 119-84-6(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralSkin Sens. 1 |
Anwendungen & Verwendung
Occurrence
Reported found in Melilotus officinalis, from which it may be extracted by water distillation.
Herstellung & Synthese
synthetische
Dihydrocoumarin is synthesized by reduction of coumarin under pressure in the presence of nickel at 160 to 200°C or in the presence of Pd-BaSO4 in alcoholic solution.