Hydroxycitronellal

HCID 7888

Basic information

CAS
107-75-5
Standard SMILES
CC(CC=O)CCCC(C)(C)O
InChIKey
WPFVBOQKRVRMJB-UHFFFAOYSA-N
Molecular formula
C10H20O2
Average molar mass
172.26 g/mol
Monoisotopic mass
172.14632988

Overview

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.

Names & identifiers

Preferred name
Hydroxycitronellal
IUPAC
7-hydroxy-3,7-dimethyloctanal
English name
3,7-Dimethyl-7-hydroxyoctanal
Molecular formula
C10H20O2
Molecular weight
172.26

Names & synonyms

Hydroxycitronellal7-Hydroxy-3,7-dimethyloctanal107-75-57-Hydroxycitronellal3,7-Dimethyl-7-hydroxyoctanalCitronellal hydratePhixiaCyclaliaCyclosiaLaurineFixolLilyl aldehyde
Show more names
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

Database identifiers

CAS
107-75-5
PubChem CID
7888
DTXSID
DTXSID6042232
ChEMBL
CHEMBL3186027
ChEBI
CHEBI:53459
UNII
8SQ0VA4YUR
EC Number
203-518-7
Nikkaji
J2.859B

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
6
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
Cosmetics · 2 items

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

Physicochemical properties

Melting point
22 · 22-23 °C
Boiling point
257 °C · 257 °C(lit.)
Density
0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
vapor pressure
0.547 Pa · 0.547Pa at 20℃
FEMA
2583 · 2583 | HYDROXYCITRONELLAL
refractive index
20 · n20/D 1.448(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 5 items

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 · 1 item

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 · 3 items

Skin Sens. 1 (> 99.9%)

Eye irritation - category 2A

Serious eye damage/eye irritation - Category 2

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
RG7850000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29124990

Chemistry & industry

Pharmacology

Biological Half-LifeThe mean elimination half-life has been found to be 3.3 h.
Metabolism/Metabolites · 1 item

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 · 6 items

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

Uses & manufacturing

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 · 6 items

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 · 2 items

Cosmetics product ingredient: Hydroxycitronellal (7-Hydroxycitronellal)

Information on 159 consumer products that contain Hydroxycitronellal in the following categories is provided:

Applications · 4 items

DescriptionHydroxycitronellal 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

UsesHydroxycitronellal 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).

Uses7-Hydroxycitronellal shows fungicide activity the strains of Candida tropicalis.

Preparation methods · 1 item

PreparationThe 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].

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

Additional notes

DefinitionChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.

Related reactions

7 records

Compound notes

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