시트로넬랄
3,7-디메틸-6-옥텐-1-알 · 시트로넬랄 · 시트로넬알 · Citronella · RHODINAL · 3,7-dimethyloct-6-enal · 3,7-DIMETHYL-6-OCTENAL · (+/-)-CITRONELLAL
식별자 및 물리적 특성
| CAS No. | 106-23-0 |
|---|---|
| 분자식 | C10H18O |
| 평균 분자량 | 154.25 g/mol |
| 단동위원소 질량 | 154.13576519 g/mol |
| SMILES | CC(C)=CCCC(C)CC=O |
| InChIKey | NEHNMFOYXAPHSD-UHFFFAOYSA-N |
| PubChem CID | 7794 |
| ChEMBL | CHEMBL1081721 |
| ChEBI | CHEBI:47856 |
| EC No. | 203-376-6 |
| DTXSID | DTXSID3041790 |
| 현지명 | 시트로넬랄 |
화학 및 물리적 성질
| XLogP | 3 |
|---|---|
| 극성 표면적 | 17.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 132 |
| 냄새 | Intense lemon-citronella-rose odor디프로필렌 글리콜 중 10.00%. 달콤한 드라이 꽃무늬 허브 밀랍 알데히드 감귤류 |
| 밀도 | 0.853 g/cu cm at 20 °C0.850-0.8600.857 g/mL at 25 °C(lit.) |
| Color/Form | Needles or orthorhombic crystalsColorless to slightly yellow liquid |
| 용해도 | Slightly soluble in waterSoluble in ethanolInsoluble in water, glycerolslightly soluble in propylene glycolsoluble in fixed oilssoluble (in ethanol)클로로포름(수용성), 메탄올(소량으로 용해) |
| 인화점 | 165 °F (74 °C) (CLOSED CUP)169 °F |
| 끓는 점 | 205 °C206.00 to 207.00 °C. @ 760.00 mm Hg206 °C207 °C(lit.) |
| 녹는점 | 147 °C-16°C (estimate) |
| 증기압 | 0.28 [mmHg]VP: 5 mm Hg, temp not specified14 hPa (88 °C) |
| Optical Rotation | Specific optical rotation: +13.09 deg at 18 °C/Dmax absorption (alcohol): 235 nm (log e = 1.93)290 nm shoulder (log e = 1.08) /d-Citronellal/Specific optical rotation: +11.50 deg at 25 °C/DSpecific optical rotation: -1 to +11 deg |
| 굴절률 | Index of refraction: 1.446 at 20 °C/D1.446-1.456n20/D 1.451(lit.) |
| Physical Description | LiquidColorless to slightly yellow liquid with a strong flowery lemon odor[HSDB]Solidcolourless to slightly yellow liquidintense lemon-citronella-rose aroma |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| FEMA | 2307 | CITRONELLAL |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | 액체 |
| 비중 | 0.858 (20/4℃) |
| 색상 | 맑은 연한 노란색 |
| pH | 7 (H2O) |
| 향취 유형 | 꽃향기 |
| 생물학적 소스 | synthetic |
| 폭발한계 | 1.2-4.5%(V) |
| 용해도 | 물과 에탄올과 약간 섞입니다. |
| Merck | 14,2329 |
| JECFA Number | 1220 |
| BRN | 1720789 |
| 헨리 상수 | 2.5×10-2 mol/(m3Pa) at 25℃, Roon et al. (2005) |
| 안정성 | 흡습성 |
| 주요 응용 | 청소용품화장품향료 및 향음식 및 음료개인 위생 관리 |
| 화장품 원료 기능 | 향기 |
| InChI | 1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3 |
| InChIKey | NEHNMFOYXAPHSD-UHFFFAOYSA-N |
| SMILES | CC(CC\C=C(\C)C)CC=O |
| LogP(분배 계수) | 3.62 at 25℃ |
| NIST | 6-Octenal, 3,7-dimethyl-(106-23-0) |
| EPA | Citronellal (106-23-0) |
화학적 성질
()-Citronellal occurs in Java citronella oil at a concentration of 35%. Racemic citronellal is the main constituent of E. citriodora oil with a content of up to 85%. Pure citronellal is a colorless liquid with a refreshing odor, reminiscent of lemon balm. Upon catalytic hydrogenation, citronellal yields dihydrocitronellal, citronellol, or dihydrocitronellol, depending on the reaction conditions. Protection of the aldehyde group, followed by addition of water to the double bond in the presence of mineral acids or ion-exchange resins results in the formation of 3,7-dimethyl-7-hydroxy-octan-l-al (hydroxydihydrocitronellal). Acid-catalyzed cyclization to isopulegol is an important step in the synthesis of ()-menthol.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2050) of reports.WarningH315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (97.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (99.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H411 (77.9%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2050 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 2050 reports by companies.There are 16 notifications provided by 2049 of 2050 reports by companies with hazard statement code(s).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. |
|---|---|
| 규제 정보 | Chemical: 6-Octenal, 3,7-dimethyl-Regulation (EC) No 1831/2003 (amended)6-Octenal, 3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 6-Octenal, 3,7-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 17-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11672Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/239896-Octenal, 3,7-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | A mild irritantEmergency treatment: Lemon grass oilCitral, the main component, causes liver injury in high-dose animal experimentsCitral in concentrations >8% can cause irritation or allergic dermatitis |
용도
출처
The d-form of citronellal has been reported in the oil of citronella (Ceylon, Jammus, Kaschmis), in the oil from leaves of Barosma pulchella, in the oil from roots of Phebalium nudum and in the oils of Eucalyptus citriodora, Leptospermum citratum and Baeckea citriodora. The /-form is present in the oils of Backhousia citriodora var. A, E. citriodora, Litsea cubeba (fruits) and lemongrass. Citronellal is generally present also in the oils of lemon, mandarin, Lavandula delphinensis, Ocimum canum f. citrata and many others (Fenarolis Handbook of Flavor Ingredients, 1971).
용도
rac-Citronellal is a monoterpenoid and the major isolate in citronella oil. Citronella oil is an essential oil bearing insecticidal properties. rac-Citronellal is also often used as a fragrance ingred ient.
일반 설명
(±)-Citronellal was studied for its fumigant antifungal activity against Pyricularia (Magnaporthe) grisea.
제조 및 합성 방법
제조 방법
Citronellal is still isolated from essential oils in considerable quantities; it is also produced synthetically. 1) Isolation from essential oils:(+)-Citronellal is obtained from citronella oils by fractional distillation. Racemic citronellal is isolated from E. citriodora oil; when necessary, it is purified by using an addition compound, for example, the bisulfite derivative. 2) Synthesis from geraniol or nerol: Racemic citronellal can be obtained by vaporphase rearrangement of geraniol or nerol in the presence of, for example, a barium-containing copper–chromium oxide catalyst. 3) Synthesis from citronellol: Racemic citronellal can also be obtained by dehydrogenation of citronellol under reduced pressure with a copper chromite catalyst. 4) Synthesis from citral: Selective hydrogenation of citral to citronellal can be accomplished in the presence of a palladium catalyst in an alkaline alcoholic reaction medium. A continuously operating process for the hydrogenation on a palladium catalyst in the presence of trimethylamine has been developed. 5) Synthesis from myrcene: (+)- and ()-Citronellal are available from myrcene via geranyldiethylamine, which is enantioselectively isomerized to (+)- or ()-citronellalenamine. Hydrolysis yields pure (+)- or ()-citronellal; see monograph menthol.