7-Hydroxycitronellal
Hydroxycitronellal
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Grundinformationen
- CAS
107-75-5- Standard-SMILES
CC(CC=O)CCCC(C)(C)O- InChIKey
WPFVBOQKRVRMJB-UHFFFAOYSA-N- Summenformel
- C10H20O2
- Durchschnittliche Molmasse
- 172,26 g/mol
- Monoisotopische Masse
- 172,14632988
Überblick
Hydroxycitronellal is the tertiary alcohol arising from addition of water across the C=C double bond of citronellal. It has a role as a fragrance and an allergen. It is functionally related to a citronellal.
Namen und Bezeichner
- Bevorzugter Name
- Hydroxycitronellal
- IUPAC
- 7-hydroxy-3,7-dimethyloctanal
- Lokaler Name
- 7-Hydroxycitronellal
- Englischer Name
- 3,7-Dimethyl-7-hydroxyoctanal
- Summenformel
- C10H20O2
- Molmasse
- 172.26
Namen und Synonyme
Hydroxycitronellal7-Hydroxy-3,7-dimethyloctanal107-75-57-Hydroxycitronellal3,7-Dimethyl-7-hydroxyoctanalCitronellal hydratePhixiaCyclaliaCyclosiaLaurineFixolLilyl aldehyde
Weitere Namen anzeigen
OCTANAL, 7-HYDROXY-3,7-DIMETHYLFEMA 2583hydroxycitoronellalHYDROXYCITRONELLAL(AS)7-hydroxy-3,7-dimethyl-octana
Muguettine principleOctanal, 7-hydroxy-3,7-dimethyl-Musuettine principleOxydihydrocitronellalhydroxy citronellal1-OCTANAL, 3,7-DIMETHYL-7-HYDROXY-FEMA No. 2583DTXSID6042232
Datenbank-Bezeichner
- CAS
107-75-5- PubChem CID
- 7888
- DTXSID
DTXSID6042232- ChEMBL
CHEMBL3186027- ChEBI
CHEBI:53459- UNII
- 8SQ0VA4YUR
- EC Number
- 203-518-7
- Nikkaji
- J2.859B
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 130
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Plant Oils and Extracts
Cosmetics
Cosmetics ingredient -> Base; Flavor; Fragrance; Moisturizing/Humectant; Other (Specify)
Masking
FragrancesFragrance Ingredient (Hydroxycitronellal) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.918-0.923
Flavoring AgentsEU Flavoring substances
Solubility
slightly
slightly soluble in water; soluble in alcohol, propylene glycol, and oils; insoluble in glycerol
1 ml in 1 ml 50% alcohol (in ethanol)
Boiling Point
241.00 °C. @ 760.00 mm Hg
241 °C; 94-96 °C (1 mm Hg)
Refractive Index1.447-1.450
Physical Description
Liquid; Dry Powder; Liquid; CBI
Liquid; [Sigma-Aldrich MSDS]
colourless liquid with sweet floral lily-like odour
Physikochemische Eigenschaften
- Schmelzpunkt
- 22 · 22-23 °C
- Siedepunkt
- 257 °C · 257 °C(lit.)
- Dichte
- 0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
- Dampfdruck
- 0.547 Pa · 0.547Pa at 20℃
- FEMA
- 2583 · 2583 | HYDROXYCITRONELLAL
- Brechungsindex
- 20 · n20/D 1.448(lit.)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- Löslichkeit
- Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
- pka
- 15.31 · 15.31±0.29(Predicted)
- Aggregatzustand
- Liquid
- Wichte
- 0.93 · 0.93
- Farbe
- Clear colorless
- Geruch (Odor)
- 100 % · at 100.00 %. floral lily sweet green waxy tropical melon
- Geruchsart
- floral
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 35 g/L · 35g/L at 20℃
- JECFA Number
- 611 · 611
- Henry's Law Constant
- 9.4 · 9.4×102 mol/(m3Pa) at 25℃, Dupeux et al. (2022)
- Stabilität
- Air Sensitive
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMING
- InChI
- 1S/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3
- InChIKey
- WPFVBOQKRVRMJB-UHFFFAOYSA-N
- SMILES
- [H]C(=O)CC(C)CCCC(C)(C)O
- LogP
- 1.68 at · 1.68 at 25℃
- CAS Datenbank
- 107 · 107-75-5(CAS DataBase Reference)
- NIST chemische Informationen
- Hydroxycitronellal(107-75-5)
- EPA chemische Informationen
- 7 · Octanal, 7-hydroxy-3,7-dimethyl- (107-75-5)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2046) of reports.
Warning
H317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2046 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Gefahrenhinweise
Regulatory Information
Chemical: Octanal, 7-hydroxy-3,7-dimethyl-
Hazard Traits - Fragrance Allergen
Octanal, 7-hydroxy-3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octanal, 7-hydroxy-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: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12695
Hydroxycitronellal: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Octanal, 7-hydroxy-3,7-dimethyl-: Human health tier II assessment
Hazards Summary
A severe eye and moderate skin irritant; Causes cutaneous sensitization in 3-day intermittent dermal studies of mice; [RTECS] Fragrance ingredient that is a recognized contact allergen in consumers; [EC: SCCNFP] Safe when used as a flavoring agent in food; [JECFA] Contained in fragrance mix; [Kanerva, p. 1803] An irritant; [Sigma-Aldrich MSDS] See Citronellal.
Hazard Classes and Categories
Skin Sens. 1 (> 99.9%)
Eye irritation - category 2A
Serious eye damage/eye irritation - Category 2
Toxikologische Informationen
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29124990
- RTECS-Nr.
- RG7850000
- risk_code
- 38-41-43
- hazard_code
- Xi
- safety_code
- 26-39-36/37
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
Biological Half-LifeThe mean elimination half-life has been found to be 3.3 h.
Metabolism/Metabolites
Studies in rabbits have shown that hydroxycitronellal is converted to two primary metabolites: reduction to the alcohol 7-hydroxycitronellol and oxidation to the carboxylic acid 7-hydroxycitronellylic acid. On average, about 50% of hydroxycitronellal is excreted as 7-hydroxycitronellylic acid which is therefore regarded as the major metabolite.
FDA Pharmacological Classification
8SQ0VA4YUR
HYDROXYCITRONELLAL
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Physiologic Effects [PE] - Increased Histamine Release
Physiologic Effects [PE] - Cell-mediated Immunity
Chemical Structure [CS] - Allergens
Absorption, Distribution and ExcretionTmax was found to be 2.70 ± 1.36
Cellular LocationsCytoplasm
Verwendung und Herstellung
UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as a fragrance; [EC: SCCNFP] Used as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 8,500,000 - <10,000,000 lb
Consumer UsesFragrance
Industry UsesFragrance
IFRA Fragrance Standards
Hydroxycitronellal
Hydroxycitronellal; Citronellalhydrate; 7-Hydroxy-3,7-dimethyloctanal; 3,7-Dimethyl-7-hydroxyoctanal; Octanal, 7-hydroxy-3,7-dimethyl-; Oxydihydrocitronellal; Laurinal (commercial name); Laurine (commercial name)
IFRA_STD_043.pdf
51
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
Household Products
Cosmetics product ingredient: Hydroxycitronellal (7-Hydroxycitronellal)
Information on 159 consumer products that contain Hydroxycitronellal in the following categories is provided:
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
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Octanal, 7-hydroxy-3,7-dimethyl-: ACTIVE
Restriction Limits in the Finished Product (%)
0.38 [Products applied to the lips]
0.11 [Products applied to the axillae]
2.2999999999999998 [Products applied to the face/body using fingertips]
2.1 [Products related to fine fragrances]
0.53 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
0.53 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
Anwendungen
BeschreibungHydroxycitronellal has an intense, sweet, floral, lily-type odor. It may be prepared by hydration of natural citronellal obtained from Java citronella or from Eucalyptus citriodora; P-pinene is converted to myrcene, which on hydration may yield either linalool or a mixture of geranoil and nerol; the latter mixture can be hydrogenated to citronellol and subsequently converted to citronellal and hydroxycitronellal; also by hydrogenation of 3,7-dimethyl- 7-hydroxy-2-octen-2-al over palladium carbon in ethyl acetate solution.
OccurrenceReported found in pepper
VerwendenHydroxycitronellal is a fragrance for use in various perfumes, antiseptics, insecticides and household products; some perfumery uses (sweet pea Pois De Senteur; gardenia; cherry; melon; mint).
Darstellung
synthetischeThe most important synthetic routes to hydroxydihydrocitronellal are listed as follows. 1) Synthesis from citronellal: One of the oldest routes to hydroxydihydrocitronellal is the hydration of the citronellal bisulfite adduct (obtained at low temperature) with sulfuric acid, followed by decomposition with sodium carbonate. A more recent development is hydration of citronellal enamines or imines, followed by hydrolysis. 2) Synthesis from citronellol. Citronellol is hydrated to 3,7-dimethyloctane-1,7- diol, for example, by reaction with 60% sulfuric acid. The diol is dehydrogenated catalytically in the vapor phase at low pressure to give highly pure hydroxydihydrocitronellal in excellent yield.The process is carried out in the presence of, for example, a copper–zinc catalyst; at atmospheric pressure, noble metal catalysts can also be used. 3) Synthesis from 7-hydroxygeranyl/-neryl dialkylamine: The starting material can be obtained by treatment of myrcene with a dialkylamine in the presence of an alkali dialkylamide, followed by hydration with sulfuric acid. The 7-hydroxygeranyl/-neryl dialkylamine isomerizes to the corresponding 7-hydroxyaldehyde enamine in the presence of a palladium(II)- phosphine complex as catalyst. Hydrolysis of the enamine gives 7-hydroxydihydrocitronellal [151].
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.
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