기본 정보
- CAS
122-48-5- 표준 SMILES
COc1cc(CCC(C)=O)ccc1O- InChIKey
OJYLAHXKWMRDGS-UHFFFAOYSA-N- 분자식
- C11H14O3
- 평균 분자량
- 194.23 g/mol
- 단동위원소 질량
- 194.0942943
개요
Zingerone is a methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger. It has a role as an antioxidant, a flavouring agent, a fragrance, an antiemetic, a radiation protective agent, an anti-inflammatory agent and a plant metabolite. It is a monomethoxybenzene, a member of phenols and a methyl ketone.
이름 및 식별자
- 우선 이름
- Zingerone
- IUPAC
- 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
- 영어명
- Vanillylacetone
- 분자식
- C11H14O3
- 분자량
- 194.23
이름 및 동의어
ZINGERONEVanillylacetone122-48-54-(4-Hydroxy-3-methoxyphenyl)butan-2-oneZingiberone4-(4-Hydroxy-3-methoxyphenyl)-2-butanoneZingheroneGingeroneVanillyl acetone2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-[0]-Paradol4-Hydroxy-3-methoxybenzylacetone
이름 더 보기
FEMA 3124ZingaroneNSC 15335
3-Methoxy-4-hydroxybenzylacetone(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone(0)-Paradol4-(3-Methoxy-4-hydroxyphenyl)-2-butanoneFEMA No. 3124DTXSID80474202-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketoneNSC-15335
데이터베이스 식별자
- CAS
122-48-5- PubChem CID
- 31211
- DTXSID
DTXSID8047420- ChEMBL
CHEMBL25894- ChEBI
CHEBI:68657- UNII
- 4MMW850892
- EC Number
- 204-548-3
- Nikkaji
- J5.356B
물성
구조 계산 물성
- XLogP
- 0.8
- 극성 표면적
- 46.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 14
- 형식 전하
- 0
- 복잡도
- 191
실험 및 물리화학적 성질
Chemical ClassesOther Uses -> Food Additives
FragrancesFragrance Ingredient (Zingerone) -> IFRA transparency List
Odor
STRONG, PUNGENT ODOR REMINISCENT OF GINGER
SWEET, SPICY AROMA
Taste
SHARP TASTE SIMILAR TO GINGER
SWEET, SPICY TASTE
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.138-1.139 @ 25 °C
Flavoring AgentsEU Flavoring substances
Color/FormCrystals from acetone, petroleum ether, ether plus petroleum ether
Solubility
Sparingly sol in water, petroleum ether; sol in ether, dil alkalies
Very soluble in ethyl ether
SOLUBILITY 1:1 IN 50% ALCOHOL
slightly soluble in water
moderately soluble (in ethanol)
Flash PointAPPROX 102 °C
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 99.4% (1413 of 1421) of all reports.
Not Classified
Aggregated GHS information provided per 1421 reports by companies from 4 notifications to the ECHA C&L Inventory.
유해성 정보
Regulatory Information
Chemical: 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-
Regulation (EC) No 1831/2003 (amended)
2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-: Environment tier I assessment
Hazards SummaryOral LD50 (rat) = 2580 mg/kg; [HSDB] An irritant; [MSDSonline]
FDA Requirements
Zingerone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
OF DIRECT FOOD ADDITIVES- LIMITATIONS: SYNTHETIC FLAVOR.
Hazard Classes and CategoriesNot Classified
안전 및 보호
Disposal Methods
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.
화학 및 산업
약리 정보
Metabolism/Metabolites
ORAL OR IP ADMIN OF 100 MG/KG /TO RATS/ RESULTED IN URINARY EXCRETION...MAINLY AS GLUCURONIDE AND/OR SULFATE CONJUGATES. WHILST UNCHANGED ZINGERONE ACCOUNTED FOR 50-55% OF DOSE, REDN TO CARBINOL (11-13%) ALSO OCCURRED.
/AFTER ORAL OR IP ADMIN OF 100 MG/KG ZINGERONE TO RATS/ SIDE CHAIN OXIDN TOOK PLACE AT THE 3 FEASIBLE SITES, AND OXIDN IN 3-POSITION PREDOMINATED TO YIELD C-6--C-2 METABOLITES. IDENTIFIED METABOLITES ACCOUNTED FOR 95-97% OF DOSE.
BILIARY STUDIES AND INVESTIGATIONS WITH CECAL MICRO-ORGANISMS IN VITRO /IN RATS/ INDICATED THAT SEVERAL OF THE URINARY O-DEMETHYLATED METABOLITES /OF ZINGERONE/ WERE OF BACTERIAL ORIGIN.
Cellular LocationsCytoplasm
용도 및 제조
Uses
Obtained from ginger root or prepared from vanillin and acetone; Used in fragrances, flavors, cosmetics, and spice oils; [Merck Index]
FLAVOR INGREDIENT
Flavoring
Methods of Manufacturing
Isolated from ginger root or prepared from vanillin and acetone followed by catalytic hydrogenation: Nomura, J Chem Soc 111, 769 (1917); Nomura, US patents 1,263,796 (1918), 1,306,710 (1919); Cotton, US patent 2,381,210 (1945 to Penn Coal Prod Co).
Formulations/PreparationsCOMMERCIAL PRODUCT CONTAINS A MINIMUM OF 93% ZINGERONE.
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
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