메틸(2-)-2-헵텐-6-온
6-메틸-5-헵텐-2-온 · 메틸(2-)-2-헵텐-6-온 · METHYL HEPTENONE · sulcatone · 6-METHYL-5-HEPTENE-2-ONE · 2-METHYL-2-HEPTEN-6-ONE · FEMA 2707 · methyl-5-hepten-2-one
식별자 및 물리적 특성
| CAS No. | 110-93-0 |
|---|---|
| 분자식 | C8H14O |
| 평균 분자량 | 126.2 g/mol |
| 단동위원소 질량 | 126.10446507 g/mol |
| SMILES | CC(=O)CCC=C(C)C |
| InChIKey | UHEPJGULSIKKTP-UHFFFAOYSA-N |
| PubChem CID | 9862 |
| ChEMBL | CHEMBL46340 |
| ChEBI | CHEBI:16310 |
| EC No. | 203-816-7 |
| DTXSID | DTXSID5021629 |
| 현지명 | 메틸(2-)-2-헵텐-6-온 |
화학 및 물리적 성질
| XLogP | 1.9 |
|---|---|
| 극성 표면적 | 17.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 119 |
| 물질 분류 | Other Classes -> Aliphatic Ketones, Other |
| 지질 | Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12] |
| SpringerMaterials Properties | Boiling point |
| 향료 | Fragrance Ingredient (6-Methyl-5-hepten-2-one) -> IFRA transparency ListFragrance Ingredient (Methylheptenone (isomer unspecified)) -> IFRA transparency List |
| 냄새 | POWERFUL, FATTY, GREEN, CITRUS ODOR디프로필렌 글리콜 중 10.00%. 감귤류 녹색 곰팡이 레몬그라스 사과 |
| 맛 | FRUITY TASTE |
| 식품 첨가물 | FLAVOR ENHANCER -> FDA Substance added to food |
| 밀도 | 0.8546 @ 16 °C/4 °C0.846-0.8540.855 g/mL at 25 °C(lit.) |
| 향미제 | EU Flavoring substances |
| Color/Form | COLORLESS LIQUID |
| 용해도 | INSOL IN WATERSOL IN ALL PROP WITH ALCOHOL, ETHER3351 /mg/L @ 20 °C (exp)Insoluble in watersoluble in oils and organic solventsMiscible at room temperature (in ethanol)메탄올과 클로로포름에 용해됩니다. |
| 인화점 | 135 °F (57 °C)123 °F |
| 녹는점 | -67.1 °C |
| 끓는 점 | 73 °C18 mm Hg(lit.) |
| 증기압 | 1.121hPa at 20℃ |
| FEMA | 2707 | 6-METHYL-5-HEPTEN-2-ONE |
| 굴절률 | n20/D 1.439(lit.) |
| 저장 조건 | Sealed in dry,2-8°C |
| 물리적 상태 | Liquid |
| 색상 | 무색~연황색 |
| 비중 | 0.855 |
| pH | 6.6 (3g/l, H2O, 25℃) |
| 향취 유형 | 감귤류 |
| 생물학적 소스 | synthetic |
| 폭발한계 | 1.1-7.3%(V) |
| 용해도 | 불용성 |
| JECFA Number | 1120 |
| BRN | 1741705 |
| 헨리 상수 | 1.2×10-1 mol/(m3Pa) at 25℃, Wu et al. (2022) |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 향수 |
| InChI | 1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3 |
| InChIKey | UHEPJGULSIKKTP-UHFFFAOYSA-N |
| SMILES | C\C(C)=C\CCC(C)=O |
| LogP(분배 계수) | 2.07 at 25℃ |
| NIST | 5-Hepten-2-one, 6-methyl-(110-93-0) |
| EPA | 6-Methyl-5-hepten-2-one (110-93-0) |
화학적 성질
6-Methyl-5-hepten-2-one is an important intermediate in the synthesis of terpenoids. Its odor properties are not impressive. It occurs in nature as a degradation product of terpenes. (Z)- and (E)-Tagetone, [3588-18-9], [6752-80-3], are major components of tagetes oil. Solanone [1937-54-8] and pseudoionone [141-10-6] are acyclicC13 ketoneswith a terpenoid skeleton. Solanone is one of the flavor-determining constituents of tobacco, and pseudoionone is an intermediate in the synthesis of ionones.
안전 및 규제
| GHS 분류 | WarningH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1822 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1601) of reports. |
|---|---|
| 규제 정보 | Chemical: 5-Hepten-2-one, 6-methyl-Chemical: Heptenone, methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 27-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/122055-Hepten-2-one, 6-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | No sensitization when patch testing 3% in petrolatum on 25 volunteers[HSDB]No skin sensitization observed in study of 25 volunteers[IUCLID] Mild skin irritation observed in rabbits (nearly reversed in 48 hours)Causes mild corneal opacity and mild conjunctival redness in rabbits 24 hours following application (completely reversed within 8 days)Not a skin sensitizer in guinea pigsSignificant effects to sperm, significantly increased absolute and relative liver and kidney weights, decreased size of the testes and epididymis, and histopathological changes of the liver, kidney, and testes observed in 90-day oral study of rats at the highest tested dose (1,000 mg/kg/day, with a LOAEL of 50 mg/kg/day)[OECD SIDS] Safe when used as a flavoring agent in food[JECFA] May cause irritation[Sigma-Aldrich MSDS] |
| FDA 요건 | 21 CFR 172.515SYNTHETIC FLAVOR & ADJUVANTS USEFUL IN CITRUS, BANANA, PEAR, BERRY21 CFR 121.1164 |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air. |
용도
개요
6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor, and a bittersweet taste reminiscent of pear. May be prepared from oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2C 03, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methylbuten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester.
출처
Originally identified in lemongrass; it has been reported found in the essential oils of palmarosa, lemon, citronella, vervain, geranium, Ocimum canum, Artemisia scoparia, Urtica dioica and others. Also reported found in apple, apricot, sweet and sour cherry, orange juice, citrus peel oils, bilberry, lingonberry, cranberry, guava, grapes, melon, peach, pear, raspberry, strawberry, blackberry, carrot, celery, tomato, potato, clove bud and leaf, ginger, peppermint oil, thymus, Gruyere cheese, butter, beef, hop oil, beer, cognac, cider, white wine, cocoa, tea, peanut oil, avocado, Arctic bramble, cloudberry, olive, passion fruit, plumcot, rose apple, marjoram, starfruit, mango, fig, rice, rice bran, quince, origanum, calamus, buckwheat, corn oil, wort, dried bonito, elderberry, cherimoya, kiwifruit, mountain papaya, endive, lemon balm, clary sage, nectarine, clam, Cape gooseberry, maté, German chamomile oil and mastic gum leaf oil, lime oil and apple brandy
용도
Organic synthesis, inexpensive perfumes, fla-voring.
일반 설명
6-Methyl-5-hepten-2-one is one of the main flavor volatile of tomatoes.
제조 및 합성 방법
제조 방법
From oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2CO3, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methyl-buten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester