基本情報
- 標準SMILES
CC(C)=CCCC(C)CCO- InChIKey
QMVPMAAFGQKVCJ-UHFFFAOYSA-N- 分子式
- C10H20O
- 平均分子量
- 156.26 g/mol
- 単同位体質量
- 156.15141526
概要
Citronellol is a monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. It has a role as a plant metabolite.
名称と識別子
- 優先名称
- Citronellol
- IUPAC
- 3,7-dimethyloct-6-en-1-ol
- 現地名
- β-シトロネロール
- 英語名
- Citronellol
- 分子式
- C10H20O
- 分子量
- 156.27
名称と別名
名称をさらに表示
データベース識別子
- CAS
106-22-9、26489-01-0- PubChem CID
- 8842
- DTXSID
DTXSID3026726- ChEMBL
CHEMBL395827- ChEBI
CHEBI:50462- UNII
- 565OK72VNF
- EC Number
- 203-375-0、247-737-6
- Nikkaji
- J3.238G
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 20.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 5
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 112
実験および物理化学的性質
Cosmetics
Cosmetics ingredient -> Base; Flavor; Fragrance; Moisturizing/Humectant; Other (Specify)
Masking
Fragrances
Fragrance substance (Citronellol) -> IFRA amendment 49
Fragrance Ingredient (6-Octen-1-ol, 3,7-dimethyl-,(+/-)-) -> IFRA transparency List
Fragrance Ingredient (dl-Citronellol) -> IFRA transparency List
Odor
Fresh rosy odor
Rose odor
Taste
Bitter taste /d-Citronellol/; sweet, peach-like flavor /l-citronellol/
Taste characteristics at 20 ppm: floral, rose, sweet and green with fruity citrus nuances
Density
0.8550 g/cu cm at 20 °C
0.850-0.860
Solubility
In water, 200 mg/L at 25 °C
In water, 307 mg/L at 25 °C; 300 mg/L at 20 °C
Soluble in fixed oils, propylene glycol; insoluble in glycerin
Miscible in ethanol and ether /(+)-citronellol/; very soluble in ethanol and ether /(-)-citronellol/
Insoluble in glycerol; slightly soluble in water; soluble in most fixed oils, propylene glycol
soluble (in ethanol)
物理化学的性質
- 融点
- 77 · 77-83 °C(lit.)
- 沸点
- 225 °C · 225 °C(lit.)
- 比旋光度
- -0.3 · -0.3~+0.3°(D/20℃)(neat)
- 比重(密度)
- 0.857 g/mL · 0.857 g/mL at 25 °C(lit.)
- 蒸気密度
- 5.4 · 5.4 (vs air)
- 蒸気圧
- 0.02 mm · ~0.02 mm Hg ( 25 °C)
- 屈折率
- 20 · n20/D 1.456(lit.)
- FEMA
- 2309 · 2309 | DL-CITRONELLOL
- 闪点
- 209 °F · 209 °F
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- Chloroform, Methanol (Sparingly)
- 酸解離定数(Pka)
- 15.13 · 15.13±0.10(Predicted)
- 外見
- 液体
- 色
- ほとんど無色透明
- 臭い (Odor)
- 100 %で。フローラル · 100.00%で。フローラル レザー ワックスのようなバラのつぼみ 柑橘系の香り
- においのタイプ
- 花柄
- 由来生物
- synthetic
- 水溶解度
- わずかに溶ける
- Merck
- 14 · 14,2330
- JECFA Number
- 1219 · 1219
- BRN
- 1721507 · 1721507
- Henry's Law Constant
- 5.2 · 5.2×100 mol/(m3Pa) at 25℃, Martins et al. (2017)
- 安定性
- 安定。酸化剤と相容れない。
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 香料
- InChI
- 1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
- InChIKey
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N
- SMILES
- CC(CCO)CC\C=C(\C)C
- LogP
- 3.41 at · 3.41 at 25℃
- CAS データベース
- 106 · 106-22-9(CAS DataBase Reference)
- NISTの化学物質情報
- 6 · 6-Octen-1-ol, 3,7-dimethyl-(106-22-9)
- EPAの化学物質情報
- Citronellol (106-22-9)
化学的性質
化学的特性シトロネロールはレモングラスローズゼラニウムなどの植物に自然に含まれている芳香族化合物の一種です化学式はC10H18Oで主に2つの異性体すなわちシトロネロールEゲラニオールとシトロネロールZネロールの形で存在しますこの物質は香料化粧品アロマセラピーおよび蚊よけ製品に広く利用されています
化学的特性Citronellol has a characteristic rose-like odor. Because odor plays such an important part in selecting this material, there may be special grades of citronellol that do not meet the Essential Oil Association specification. These limits have been broadened enough to include best qualities of commercial citronellol and chemically pure citronellol. l-Citronellol has a sweet, peach-like flavor; d-citronellol has a bitter taste.
化学性质新鮮なバラ様
安全と法規制
GHS分類
GHS Classification
Warning
H315 (95.7%): Causes skin irritation [Warning Skin corrosion/irritation]
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 1657 reports by companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
危険有害性情報
Regulatory Information
Chemical: 6-Octen-1-ol, 3,7-dimethyl-
Regulation (EC) No 1831/2003 (amended)
6-Octen-1-ol, 3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 6-Octen-1-ol, 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: 02-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14242
Citronellol: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes degenerative changes to brain, dermatitis, changes in liver and kidney weights, and somnolence in acute oral studies of rats; Causes alteration of classical conditioning and abnormal liver function tests in 100-day inhalation studies of rats; [RTECS] A moderate skin irritant; Category members and supporting chemicals demonstrate skin sensitization in humans and mice; No systemic toxicity in 112-day and 17-week oral studies of rats at the highest tested doses (approximately 500 mg/kg/day); Mortality, stomach lesions, and cytoplasmic vacuolization (lipidosis) of the liver, kidney, and myocardium in 13-week oral study of mice (LOAEL of 2,000 mg/kg/day); [EPA ChAMP: Terpenoid Primary Alcohols and Related Esters - 2009] Fragrance ingredient that is a recognized contact allergen in consumers; [EC: SCCNFP] Generally regarded as safe (GRAS) by the FDA; [ToxPlanet: EPA BRADs] Safe when used as a flavoring agent in food; [JECFA] An irritant; [Acros Organics MSDS]
FDA Requirements
Citronellol 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 b) 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.
FIFRA Requirements
Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. (a) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-contact surfaces in public eating places, dairy-processing equipment, and food-processing equipment and utensils. Citronellol is included on this list. Limit: When ready for use, the end-use concentration is not to exceed 100 ppm.
An exemption from the requirement of a tolerance is established for residues of the biochemical pesticide citronellol in or on all food commodities.
Hazard Classes and Categories
Skin Irrit. 2 (100%)
Skin Irrit. 2 (95.7%)
Skin, Eye, and Respiratory Irritations
...moderate eye irritation...
/Skin/ moderately irritating.
安全と保護具
Fire Fighting Procedures
Wear self-contained breathing apparatus for firefighting if necessary.
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Cleanup Methods
ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.
Disposal Methods
SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging Dispose of as unused product.
Preventive Measures
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Allowable Tolerances
Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. (a) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-contact surfaces in public eating places, dairy-processing equipment, and food-processing equipment and utensils. Citronellol is included on this list. Limit: When ready for use, the end-use concentration is not to exceed 100 ppm.
An exemption from the requirement of a tolerance is established for residues of the biochemical pesticide citronellol in or on all food commodities.
Personal Protective Equipment (PPE)
Skin protection: Handle with gloves.
Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
毒性情報
Ecotoxicity Values
LC50; Species: Leuciscus idus (Golden orfe); Conditions: static; Concentration: >10 mg/L for 96 hr
EC50; Species: Selenastrum subspicatus (Green algae); Concentration: 2.38 mg/L for 72 hr; Effect: growth /Conditions of bioassay not specified in source examined/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that citronellol is expected to have high mobility in soil(SRC). Volatilization of citronellol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(3), and water solubility, 200 mg/L(4). Even though the vapor pressure is low environmentally at standard temperature and pressure, there is a detectable odor; therefore, citronellol may volatilize from dry soil(SRC). An 80-90% of Theoretical BOD using activated sludge in the OECD 301F test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). Citronellol was also classified as readily biodegradable by the results of the OECD 301C test (modified MITI) with 65% degradation in 4 weeks(6) and by a DOC Method F test (100% biodegradation in 15 days)(6). Citronellol absorbs at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that citronellol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(4), and water solubility, 200 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 and 21 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 177(SRC), from its log Kow of 3.91(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). An 80-90% of Theoretical BOD using activated sludge in the OECD 301F test(8) suggests that biodegradation is an important environmental fate process in water(SRC). Citronellol was also classified as readily biodegradable by the results of the OECD 301C test (modified MITI) with 65% degradation in 4 weeks(9) and by a DOC Method F test (100% biodegradation in 15 days)(9). Citronellol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Citronellol is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), citronellol, which has a vapor pressure of 0.02 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase citronellol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.3 hours(SRC), calculated from its rate constant of 1.70X10-10 cu cm/molecule-sec at 24 deg(3). Citronellol is also degraded in the atmosphere by reaction with ozone and nitrate radicals. The half-life for the reaction with ozone is estimated to be 1.1 hours(SRC), calculated from its rate constant of 2.4X10-16 cu cm/molecule-sec at 24 °C(3). The half-life for the reaction with nitrate radicals is estimated to be 4 minutes(SRC), calculated from its rate constant of 1.21X10-11 cu cm/molecule-sec at 24 °C(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5), therefore, night-time degradation appears to be a major fate process for citronellol(SRC). Citronellol absorbs at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Toxicity Summary
IDENTIFICATION AND USE: Citronellol has been found in nature, and it has been reported in about 70 essential oils. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is also used in perfumery. HUMAN EXPOSURE AND TOXICITY: Adult male volunteers with no known allergic reactions were patch-tested on their back for 48 hr with 32% citronellol. After 48 hr, patches were removed and the skin was cleaned of any residual test material. Moderate irritation was observed. A patch test using a 1% concentration of citronellol in acetone gave a positive reaction in subjects allergic to citronella oil. ANIMAL STUDIES: Citronellol applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was moderately irritating. Severe irritation was observed in rabbits and guinea pigs exposed to 100% compound (unoccluded) for 24, 48 or 72 hr. Citronellol was not mutagenic when tested in Salmonella typhimurium strains TA98 and TA100 in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: Golden Orfe (Leuciscus idus) were exposed to this chemical under static conditions for 96 hours. No mortalities were seen in the control and 4.64 mg/L groups. At 10 mg/L, apathy was noted up to 24 hr, but no mortalities were noted at 96 hr. At 21.5, 46.4 and 100 mg/L, 100% mortality was seen 1 hour after exposure.
Ecotoxicity Excerpts
/AQUATIC SPECIES/ Golden Orfe (Leuciscus idus) were exposed to nominal concentrations of 0, 4.64, 10, 21.5, 46.4 or 100 mg/L of this chemical under static conditions for 96 hours. No mortalities were seen in the control and 4.64 mg/L groups. At 10 mg/L, apathy was noted up to 24 hours, but no mortalities were noted at 96 hours. At 21.5, 46.4 and 100 mg/L, 100% mortality was seen 1 hour after exposure. 96-hr LC50 > 10 mg/L
Plant Concentrations
(+)-Citronellol occurs in natural oils from Boronia citriodora (total citronellol content about 80%) and Eucalyptus citriodora (total citronellol content 15-20%)(1); (-)-Citronellol is the predominant enantiomer in geranium and rose oils, both of which may contain up to 50% citronellols(1). Citronellol has reported to occur in about 70 essential oils(2). It reportedly occurs in guava fruit, orange, bilberry, blackcurrant, nutmeg, ginger, corn, mint oil, mustard, hop oil, tea, coriander seed, and cardamom(2). Essential oils from twigs and needles of the Balkan pine (Pinus peuce Gris.) grown in northern Greece was found to contain citronellol in the twig oil (12.48% of total) and needle oil (13.42% of total)(3). Trace concentrations of citronellol (<20 ug/kg) were detected in the flowers of Japan honeysuckle (Lonicera japonica)(4). Citronellol has been detected in tobacco(5). The essential oil of rose water, derived from Rosa damascena Mill. from northern India, contained citronellol at concentrations of 15.9-35.3%(6).
Citronellol detections in plants(1).[Table#6301]
Ongoing Test Status
EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]
Effluent Concentrations
Citronellol is emitted into the ambient air from household products such as pine-oil based cleaners, orange oil-based degreasers and plug-in air fresheners(1). Citronellol was detected in volatile emissions from the leaves of Eucalyptus citriodora(2).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of citronellol can be estimated to be 94(SRC). According to a classification scheme(2), this estimated Koc value suggests that citronellol is expected to have high mobility in soil.
Natural Pollution Sources
Citronellol is widespread in nature in both enantiomeric forms, the richest sources being rose and geranium(1). Citronellol is reported to occur in about 70 essential oils(2). Citronellol has been detected and quantified in numerous plant species(3).
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ The fragrance mix (FM I), established in 1977, detects the majority, but not all cases of contact allergy to fragrances. Based on European research 2002/2003, fragrance mix II (FM II) was developed to supplement FM I. In 2005, the German Contact Dermatitis Research Group (DKG) added FM II to their baseline series. /The objective was/ to evaluate reactions to FM II and its constituents in routine patch testing. Retrospective data analysis of the Information Network of Departments of Dermatology (IVDK), 2005-2008, of patch test results with FM II and its constituents. A total of 35,633 patients were patch tested with FM II as part of the DKG baseline series. Of these, 1742 (4.9%) reacted positively. Concomitant reactions to FM I were observed in 41.9% of the patients reacting to FM II. In 367 FM II-positive patients, a full breakdown test of the mix was performed. Of these, 47.7% reacted to hydroxyisohexyl 3-cyclohexene carboxaldehyde, 16.1% to citral, 11.4% to farnesol, 3.8% to hexyl cinnamal, 2.7% to coumarin, and 2.5% to citronellol. FM II is an important screening and diagnostic tool to detect fragrance allergy. Hydroxyisohexyl 3-cyclohexene carboxaldehyde is the most important fragrance allergen in FM II.
/HUMAN EXPOSURE STUDIES/ Fragrance mix II (FM II) was initiated to detect contact hypersenstitivity (CH) to fragrances that could not have been identified previously. OBJECTIVE: The aim of this multicenter study was to map the frequency of CH to FM II and its components in Hungary. METHODS: Six centers participated in the survey from 2009 to 2010. A total off 565 patients (434 women and 131 men) with former skin symptoms provoked by scented products were patch tested. The tests were performed with Brial GmbH D-Greven allergens. In the environmental patch test series, FM II, FM I, Myroxylon pereirae, colophonium, wood-tar mix, propolis, and sesquiterpene lactone mix were tested as fragrance allergens. The FM II components (citral, farnesol, coumarin, citronellol, alpha-hexyl-cinnamaldehyde, and hydroxy-isohexyl-3-cyclohexene-carboxaldehyde [Lyral]) were also tested. RESULTS: Contact hypersenstitivity to any fragrances was detected in 28.8%, to FM II in 17.2% of the patients. Contact hypersenstitivity to hydroxy-isohexyl-3-cyclohexene-carboxaldehyde was observed in 7.3%, to coumarin in 5.1%, to alpha-hexyl-cinnamaldehyde in 3.5%, to citral in 3.4%, to farnesol in 2.5%, and to citronellol in 1.2%. Of the FM II-positive cases, 48.4% showed isolated CH reaction. CONCLUSIONS: The frequency of CH to FM II is 17.2% in the tested, selected Hungarian population. The CH to FM II and its components could not have been revealed without the present test materials.
/HUMAN EXPOSURE STUDIES/ A 24-hr patch test using full strength citronellol produced no irritation reactions in 20 subjects.
/HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 6% in petrolatum and produced no sensitization reactions.
For more Human Toxicity Excerpts (Complete) data for Citronellol (6 total), please visit the HSDB record page.
法規制情報
FDA Requirements
Citronellol 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 b) 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.
FIFRA Requirements
Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. (a) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-contact surfaces in public eating places, dairy-processing equipment, and food-processing equipment and utensils. Citronellol is included on this list. Limit: When ready for use, the end-use concentration is not to exceed 100 ppm.
An exemption from the requirement of a tolerance is established for residues of the biochemical pesticide citronellol in or on all food commodities.
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RH3400000
- 毒性
- The acute oral LD50 value in rats was reported as 3.45 g/kg (3.21-3.69 g/kg) (Moreno, 1973). The acute dermal LE>50 value in rabbits was reported as 2.65 g/kg (1.78-3.52 g/kg) (Moreno, 1973). The im LD50 value in mice was reported as 4 g/kg (Northover & Verghese, 1962).
- hs_code
- 29052220
- risk_code
- 36/37/38-51/53-43-36/38
- 化審法
- (2)-258
- 消防法
- 危-4-3-III
- hazard_code
- Xi,N
- hazard_note
- Irritant
- safety_code
- 26-36-24/25-61-37-24
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1B
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 106-22-9(Hazardous Substances Data)
化学と産業
薬理情報
Mechanism of Action
We evaluated the effects of rose oil on the peroxisome proliferator-activated receptor (PPAR) and cyclooxygenase-2 (COX-2).Citronellol and geraniol, the major components of rose oil, activated PPAR alpha and gamma, and suppressed LPS-induced COX-2 expression in cell culture assays, although the PPARgamma-dependent suppression of COX-2 promoter activity was evident only with citronellol, indicating that citronellol and geraniol were the active components of rose oil.
用途と製造
Uses
l-Form: in rose and geranium oils; d-Form: in Ceylon and Java citronella oils; Used in perfumery; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA] Present in over 30 essential oils, fruits, edible plants, wine, beer, and black tea; Active ingredient in pesticide used to control mites on agricultural crops, ornamentals, and landscapes; Also extensively used as fragrance (detergents, soaps, lotions, perfumes, etc.), as a flavoring agent, and component of citronella oil (used in candles, sprays, oils, and insect repellents); [EPA BRADs]
Farming (Pesticides) [Category: Industry]
For citronellol (USEPA/OPP Pesticide Code: 167004) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Reported uses (ppm):
In perfumery
Citronellol is one of the components responsible for the insect repellent properties of citronella oil ... Citronellol finds extensive use in floral fragrances and in flavors for citrus and other fruit notes. Its stability makes it particularly useful in fragrances for soaps, detergents, and other household products. Citronellol is also important as an intermediate in the synthesis of a number of other aroma chemicals ... Citronellol is the key feedstock for the synthesis of rose oxide.
U.S. Production
2023: 10,000,000 - <25,000,000 lb
6-Octen-1-ol, 3,7-dimethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 6-Octen-1-ol, 3,7-dimethyl-. National Production Volume: 4,727,405 lb/yr.
IFRA Fragrance Standards
Citronellol
106-22-9:; 3,7-Dimethyl-6-octen-1-ol; 6-Octen-1-ol, 3,7-dimethyl-; Citronellol; dl-Citronellol; Rhodinol pure (commercial name); 1117-61-9:; 3,7-Dimethyloct-6-en-1-ol; 6-Octen-1-ol, 3,7-dimethyl-, (R)-; (R)-3,7-Dimethyloct-6-en-1-ol; (+)-Ã-Citronellol; (+)-(R)-Citronellol; 26489-01-0:; 6-Octen-1-ol, 3,7-dimethyl-,(+/-)-; 6812-78-8:; 3,7-Dimethyloct-7-en-1-ol; 7-Octen-1-ol, 3,7-dimethyl-,(S)-; 3,7-Dimethyl-(6-or 7-)octen-1-ol; 3,7-Dimethyl-7-octen-1-ol; 141-25-3:; 3,7-Dimethyloct-7-en-1-ol; 7-Octen-1-ol, 3,7-dimethyl- (isomer unspecified); α-Citronellol; Rhodinol (commercial name); 7540-51-4:; 3,7-Dimethyloct-6-en-1-ol; (-)-3,7-Dimethyloct-6-en-1-ol; (S)-3,7-Dimethyl-6-octen-1-ol; 6-Octen-1-ol, 3,7-dimethyl-, (S)-; l-Citronellol
IFRA_STD_022.pdf
49
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Restriction: This material should be used only in the limited quantity as stated in the Standard
Methods of Manufacturing
Citronellol is manufactured on a commercial scale by the hydrogenation of nerol and geraniol, which in turn are made either from alpha- or beta-pinene. Hydrogenation of nerol and geraniol over a copper chromite catalyst gives a high yield of citronellol. Fractional distillation of the crude product produces a perfumery-quality citronellol. Geraniol can also be hydrogenated selectively to citronellol, without forming tetrahydrogeraniol, through use of a Raney cobalt catalyst. However, partial hydrogenation using a nickel catalyst does give some tetrahydrogeraniol. The product contains nerol, geraniol, and tetrahydrogeraniol and has odor properties closer to materials derived from citronella oil, and is therefore useful as a perfumery material.
Manufacturing: Woroch et al.; Bain; Webb, United States of America patent 2990422; United States of America patent 3005845; United States of America patent 3028431 (1961, 1961, 1962, all to Glidden); Eschinasi, United States of America patent 30527301962 to Givaudan).
Citronellol may be obtained by reduction of citronellal or geraniol, or by fractional distillation of geranium oil or citronella oil. It may also be prepared synthetically.
Household Products
Cosmetics product ingredient: Citronellol /+- 3,7-dimethyloct-6-en-1-ol (CITRONELLOL; (3R)-3,7-dimethyloct-6-en-1-ol; (3S)-3,7-dimethyloct-6-en-1-ol)
Information on 643 consumer products that contain Citronellol in the following categories is provided:
Use Classification
Fragrance Ingredients
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Masking
General Manufacturing Information
Not Known or Reasonably Ascertainable
6-Octen-1-ol, 3,7-dimethyl-: ACTIVE
Restriction Limits in the Finished Product (%)
2.2 [Products applied to the lips]
0.67 [Products applied to the axillae]
13 [Products applied to the face/body using fingertips]
12 [Products related to fine fragrances]
3.2 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
3.2 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
応用分野
解説C10H20O(156.26).β-シトロネロールは,非環状モノテルペンアルコール.多くの植物の精油中に含まれている."ローズ油には(-)-シトロネロールが含まれ,シトロネラ油を還元すると(+)-シトロネロールが得られる.(-)-シトロネロールはロジノール(rhodinol)ともよばれ,香料としては(+)-シトロネロールよりすぐれている.(+)-シトロネロールは沸点224.5 ℃,108.4 ℃(1.3 kPa).d2040.86.n20D1.46.[α]D+5.22°(クロロホルム).[CAS 7540-51-4:(S)-(-)シトロネロール][CAS 106-22-9:ラセミ体] 森北出版「化学辞典(第2版)
解説シトロネロールは,鎖状モノテルペンアルコールの一つ。多くの植物精油中にα-とβ-の混合物として存在する。シトロネロールには1個の不斉炭素原子があるので、右旋性(d体)、左旋性(l体)および不活性(dl体、ラセミ体)の光学異性体がある。シトロネロールはシトロネラ油、ゼラニウム油に含有され、甘いバラ様の香気を有する無色の液体である。引火点102℃。シトロネラ油を精留してシトロネロール留分をとり、精製して製品とする。シトロネラールを接触水添しても得られる。バラ、ミューゲ、スズランなどのフローラル系調合香料に用いられる。[佐藤菊正]
用途香料材料、有機合成原料。
説明Citronellol is a kind of natural occurring acyclic monoterpenoid which can be found in citronella oils such as Cymbopogon nardus ((+)-citronellol) and rose oils and Pelargonium geraniums ((-)-citronellol). In addition to be extracted from natural oils, it can also be manufactured by the hydrogenation of geraniol or nerol. It is mainly used in perfumes and insects repellents as well as being used as a mite attractant. It should be noted that it is an excellent mosquito repellent at short distances. Combination with beta-cyclodextrin can make it has an average duration time of 1.5 hour against the mosquitoes. It can also be used for the manufacture of rose oxide. One of its most common applications is for adding floral and citrus notes to perfumes, soaps and cosmetics.
天然物の起源l-Citronellol has been found in the plants of the Rosaceae family; d- and dl-citronellol have been identified in Verbenaceae, Labiatae, Rutaceae, Geraniaceae and others; citronellol has been reported in about 70 essential oils and in the oil of Rosa bourbonia; the Bulgarian rose oil has been reported to contain more than 50% l-citronellol, whereas East African geranium contains more than 80% of the d-isomer; the natural product is always optically active. Reported found in guava fruit, orange, bilberry, blackcurrant, nutmeg, ginger, corn mint oil (Mentha arvensis L. var. piperascens), mustard, pennyroyal oil (Mentha pulegium L.), hop oil, tea, coriander seed, cardamom, beer, rum, and apple juice.
使用citronellol is a constituent of plant essential oils. Found abundantly in eucalyptus oil. It is used for masking odor or providing a fragrance component to a cosmetic product.
一般的な説明Citronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolens, Cymbopogon winterianus and Rosa damascena. It is also one of the glycosidically bound aroma compounds in ginger.
調製方法
製造方法By reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967).
純化方法Purify them bydistillation through a cannon packed (Ni) column and the main cut collected at 84o/14mm and redistilled. Also purify via the benzoate. [IR: Eschenazi J Org Chem 26 3072 1961, Naves Bull Soc Chim Fr 505 1951, Beilstein 1 IV 2188.]
上流・下流製品情報
上流原料
下流製品
サプライヤー8 社
補足説明
定義本品は、次の化学式で表されるテルペンアルコールである。
定義ChEBI: A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.
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