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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 7092作成日：2026年10月27日

6-メチルクマリン

6-メチルクマリン · メチルクマリン · メチルクマリン, 6- · 6-メチルクマリン, 99% · 6-Methyl · 2H-1-BENZOPYRAN-2-ONE, 6-METHYL- · FEMA 2699 · Toncarine

https://huagongshe.com/ja/chemical/7092

6-メチルクマリン の分子構造式

識別子と物理属性

CAS No.92-48-8
分子式C10H8O2
平均分子量160.17 g/mol
単同位体質量160.05242949 g/mol
SMILESCc1ccc2oc(=O)ccc2c1
InChIKeyFXFYOPQLGGEACP-UHFFFAOYSA-N
PubChem CID7092
ChEMBLCHEMBL443436
ChEBICHEBI:563586
EC No.202-158-8
DTXSIDDTXSID9025588
現地名6-メチルクマリン

化学・物理的性質

XLogP1.8
極性表面積26.3
水素結合供与体数0
水素結合受容体数2
回転可能結合数0
重原子数12
形式電荷0
複雑度220
臭いSomewhat dry, herbaceous (tonka-like) odoralso characterized as a delicate fig or date sweetness.Coconut odorジプロピレングリコール中1.00%。ココナッツ クリーミー パウダリー クマリン トンカ シンナミル バニラ フローラル アーシー
味Almost bitter taste above 50 ppm, turning sweet and vanilla-like at lower levels.Sweet, coconut tasteVanilla flavor
Color/FormWhite, crystalline solidWhite needles from benzene
溶解度Insoluble (NTP, 1992)Very slightly sol in hot waterinsol in petroleum ethersol in oils.soluble in alcohol /both alpha and beta forms/Very soluble in ethanol, ether, benzeneslightly soluble in chloroformInsoluble in watersoluble in oilssoluble (in ethanol)DMSO : ≥ 125 mg/mL (780.42 mM)
引火点266 °F (NTP, 1992)303°C/725mm
沸点577 °F at 725 mmHg (NTP, 1992)304 °C303 °C/725 mmHg (lit.)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
融点167 to 169 °F (NTP, 1992)76.5 °CExists as alpha and beta forms, melting point(alpha): 90 °C, melting point (beta): 82 °Cboth forms are soluble in alcoholcombustible73-76 °C (lit.)
Physical Description6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992)White solid[HSDB]White crystal solidcoconut-like aroma
Kovats Retention Index15451564157415881618255125602630
Other Experimental PropertiesCongealing point: >73.5 °CUV: 375 (Sadtler Research Laboratories Spectral Collection) /Coumarin, 3-methyl/
密度1.0924 (rough estimate)
屈折率1.5300 (estimate)
FEMA2699 | 6-METHYLCOUMARIN
貯蔵条件Sealed in dry,Room Temperature
外観・状態powder to crystal
色White to Almost white
においのタイプココナッツ
由来生物synthetic
JECFA Number1172
BRN4222
主な用途フレーバーそして香料
化粧品成分の機能香料香料
InChI1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3
InChIKeyFXFYOPQLGGEACP-UHFFFAOYSA-N
SMILESCc1ccc2OC(=O)C=Cc2c1
LogP（分配係数）1.85
CAS データベース92-48-8(CAS DataBase Reference)
NISTの化学物質情報2H-1-Benzopyran-2-one, 6-methyl-(92-48-8)
EPAの化学物質情報6-Methylcoumarin (92-48-8)

化学的特性

6-methylcoumarin is a white to almost white crystalline powder with has a somewhat coconut-like odor. the odor is also characterized as having a delicate fig or date sweetness. it has an almost bitter taste above 50 ppm, turning sweet and vanilla-like at lower levels. soluble in benzene, hot ethanol and non-volatile oil, insoluble in hot water.

安全性と法規制

GHS 分類WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H319 (95%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1613 reports by companies from 4 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.
規制情報Chemical: 2H-1-Benzopyran-2-one, 6-methyl-Hazard Traits - Fragrance AllergenAuthoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance AllergensReport - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2H-1-Benzopyran-2-one, 6-methyl-: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報IMAP assessments - Coumarins: Human health tier II assessment
火災危険This chemical is combustible. (NTP, 1992)
健康有害性SYMPTOMS: This compound may cause photo-allergic reactions.ACUTE/CHRONIC HAZARDS: This compound is a mild irritant. (NTP, 1992)
有害性の概要Emergency treatment: CoumarinAfter an ingestion of 4 grams of coumarin, a patient developed muscle paralysis but no cardiovascular effectsCauses liver toxicity in rats, but humans are relatively resistantNot active as an anti-coagulant[HSDB] Causes seizures at lethal doses in mice[RTECS] Caused photoallergic contact dermatitis when it was used as a fragrance in sunscreens

用途

用途

香料・香辛料

天然物の起源

Has apparently not been reported to occur in nature

使用

6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel.

一般的な説明

6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992)

製法・合成法

製造方法

6-methylcoumarin is synthesized from p-cresol and fumaric acid. Preheat 72% sulfuric acid to 80 °C, add a mixture of fumaric acid and p-cresol, keep the reaction at 160-170 °C for 3-4 hours, cool, pour into crushed ice to precipitate a precipitate, and filter. The filtrate was extracted with benzene, and after adding benzene, the obtained crude product was subjected to vacuum distillation to obtain 6-methylcoumarin. synthesis of 6-methylcoumarin: By heating 6-methyl coumarin-3-carboxylic acid to 300 to 340°C; by condensation of p-cresol-disulfonic acid with fumaric acid in the presence of H2SO4; by condensation of p-homosalicyclic aldehyde with malonic acid in the presence of aniline, followed by heating for the lactone; from salicylaldehyde with propionic acid anhydride and sodium propionate.

When patch tested, the antigen should be applied to the skin for no longer than 30 minutes before UVA exposure because it rapidly becomes inactive. [Marks, p. 224] Safe to use as a flavoring agent in food
[JECFA] Harmful by ingestion
A photosensitizer
[Aldrich MSDS]
反応性グループEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special ReportsBIBRA working groupTA:Toxicity profile. BIBRA Toxicology International:5 (1995).
Reactivity ProfileEsters, such as 6-METHYLCOUMARIN, react with acids to liberate heat along with alcohols and acids. Generates heat with strong oxidizing acids. The reaction may be sufficiently exothermic to ignite the reaction products. Also generates heat with basic solutions. Generates flammable hydrogen with alkali metals and hydrides. Emits acrid smoke and irritating fumes when heated to decomposition.
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (100%)Eye Irrit. 2 (95%)Acute toxicity - category 4
消火Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
応急処置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)
非火災時の漏出対応SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 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 in a refrigerator. (NTP, 1992)
処分方法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)
相互作用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/
有害作用Neurotoxin - Other CNS neurotoxinDermatotoxin - PACD (photoallergic contact dermatitis).
Ongoing Test StatusThe 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=92-48-8]
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ A Maximization test was carried out on 25 human volunteers. The material was tested at a concn of 4% in petrolatum and produced no sensitization reactions./HUMAN EXPOSURE STUDIES/ 6-Methylcoumarin, a fragrance material, is a photocontact allergen./HUMAN EXPOSURE STUDIES/ The test agent is applied for 24 hr followed by exposure to 3 minimal erythema doses (med) of solar simulated radiation twice weekly for 3 wk (6 exposures) in a panel of 25 white caucasians. The subjects are challenged 2 wk later with long-wave uv radiation. 6-Methylcoumarin gave a high rate of sensitization./SPECIAL STUDIES/ ...Topical pretreatment of /human reconstituted epidermis/ (Episkin), with weak phototoxic compounds /including methyl coumarin/ induced, after UVA exposure, a dose-dependent decr in cell viability, in concordance with an increasing IL-1alpha release. Moreover, compared to chlorpromazine, the lower IL-1alpha release observed with 6-methylcoumarin and ofloxacin could be linked to their weak phototoxic potential. ...
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ 15 exposures of 6-methylcoumarin to the shoulder skin of guinea pigs that had been abraded with a nylon brush rotating @ 13,000 rpm and irradiated with broadband uv irradiation for a 3 wk induction period induced and elicited photoallergic contact dermatitis./LABORATORY ANIMALS: Acute Exposure/ More than 85% of the guinea pigs tested developed photoallergic contact dermatitis. The sensitivity could be detected in 45% of the sensitized animals using 1%, although no reaction was seen with 0.1%./LABORATORY ANIMALS: Acute Exposure/ ...Applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was mildly irritating.../LABORATORY ANIMALS: Acute Exposure/ A male dog fed 150 mg.../kg had to be killed after 39 days because of weakness, emaciation and dehydration, and showed moderate to severe hepatitis and slight to moderate muscle atrophy.For more Non-Human Toxicity Excerpts (Complete) data for METHYL COUMARIN (12 total), please visit the HSDB record page.
Antidote and Emergency TreatmentHuman exposure to second-generation and indandione anticoagulants produces symptoms consistent with anticoagulation effects (e.g., hematomas, hematemesis, hematuria, easy bruisability). Treatment of cases of exposure, particularly of substantial and repeated exposure, may require vitamin K1 therapy and monitoring of prothrombin times for periods of many months.
Non-Human Toxicity ValuesLD50 Rat oral 1,680 mg/kgLD50 Mouse subcutaneous 253 mg/kg
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号GN7792000
毒性The acute oral LD50 value in rats was reported to be 1.68 g/kg (1.43-1.93 g/kg) (Moreno, 1973). The acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno, 1973).
税関コード29321900
危険文句（R）22-42/43
化審法(5)-687
危険表示Xn
安全措置（S）22-36/37-45
危険等級Acute Tox. 4 OralResp. Sens. 1Skin Sens. 1
貯蔵分類11 - Combustible Solids
有害物質データ92-48-8(Hazardous Substances Data)