Hydroxycitronellal
Synthétique
Floral > Light Flowers > Aldehydic > Fresh Flowers > Green
Crédits photo: ScenTree SAS
Other names :
Laurinal® ; Cyclosia® ; Cyclosia Base® ; 7-hydroxy-3,7-dimethyloctanal ; Citronellal hydrate ; Citronellaldehyde ; Oxydihydrocitronellal ; Hidroxycitronellal ; 7-hydroxy-3,7-dimethyloctanal ; Lily aldehyde ; Muguet synthetic ; Muguettine principle ; Oxdihydrocitronellal
Volatility :
Heart
Uses in perfumery :
Hydroxycitronellal is used in white flowers notes: lily of the valley, lilac. Tends to be more and more restricted.
Natural availability :
Hydroxycitronellal is not available in its natural state.
Year of discovery :
Discovered in 1905.
Other comments :
Hydroxycitronellal is one of the 26 allergens in perfumery. It is also regulated by the IFRA. Therefore, it is often replaced by Florol®, which is not regulated.
Used for the first time in 1912, in Quelques fleurs by Houbigant.
Used for the first time in 1912, in Quelques fleurs by Houbigant.
Price Range :
€€
Stability :
Aldehydes may form diethylacetals in alcoholic perfumes, with no real impact on their smell.
Terpenes tend to polymerize by oxydation.
Liquefies shower gel bases.
Terpenes tend to polymerize by oxydation.
Liquefies shower gel bases.
Crédits photo: ScenTree SAS
- Molecular formula :
- C10H20O2
- Molecular Weight :
- 172,27 g/mol
- Density :
- 0,942
- Flash Point :
- 113°C
- Fusion Point :
- Donnée indisponible.
- Appearance :
- Colorless liquid
- Log P :
- 1,42
- Boiling Point :
- 257°C
- Detection Threshold :
- Donnée indisponible.
Synthesis route :
Hydroxycitronellal can be synthesized from several different reagents. The final product can be obtained from Citronellal in an acid medium and by reaction with sodium carbonate. From Citronellol, an acid hydrolysis reaction in the presence of sulfuric acid allows to obtain a diol, capable of undergoing a dehydrogenation catalysed by copper and zinc, for example. This method offers a high purity and a very good yield. From Myrcene, a reaction with a dialkylamine allows to synthesize 7-hydroxygeranyl dialkylamine, after an acid hydrolysis. After that, the presence of palladium (II) phosphine in a catalytic amount allows to change the place of the double bond in order to obtain a compound called enamine. A last acid hydrolysis of this compound allows to obtain Hydroxycitronellal.
Synthesis precursor :
Hydroxycitronellal is a precursor molecule of the synthesis of Aurantiol, by reaction with Methyl Anthranilate .
Isomerism :
Hydroxycitronellal has an asymmetric carbon that gives rise to two possible enantiomers with a similar smell.
Florol® is a constitutional isomer of Hydroxycitronellal. Both are used in particular in lily of the valley reconstructions. However, Florol® tends to replace Hydroxycitronellal in formulas, as it is not regulated.
- EINECS number :
- 203-518-7
- FEMA number :
- 2583
- JECFA number :
- 611
- FLAVIS number :
- 05.012
- Allergens :
- Hydroxycitronellal may provoke an allergic reaction on skin contact (redness, heat, scraching, prickling) for some people.
- IFRA :
- This ingredient is restricted by IFRA
- Restriction type :
- RESTRICTION
- Cause of restriction :
- DERMAL SENSITIZATION
- Amendment :
- 49
- Comments :
- This ingredient is part of the Schiff base (Hydroxycitronellal-Indole (or Indolene 50%) - N°CAS : 68527-79-7) and induces the application of IFRA regulations for 63,5% of the Schiff base usage. This ingredient is part of the Schiff base (Hydroxycitronellal methyl anthranilate (or Aurantiol, Aurantium, Aurantoin) - N°CAS : 89-43-0) and induces the application of IFRA regulations for 56,4% of the Schiff base usage. Please also refer to the IFRA Annex II for more information
- Quantitative limit on the use :
-
Cat.1 Cat.2 Cat.3 Cat.4 Cat.5A Cat.5B Cat.5C Cat.5D Cat.6 0,38 % 0,11 % 2,3 % 2,1 % 0,53 % 0,53 % 0,53 % 0,53 % 1,2 % Cat.7A Cat.7B Cat.8 Cat.9 Cat.10A Cat.10B Cat.11A Cat.11B Cat.12 4,3 % 4,3 % 0,22 % 4,1 % 15 % 15 % 8,2 % 8,2 % No Restriction - Restriction type :
- RESTRICTION
- Cause of restriction :
- DERMAL SENSITIZATION AND SYSTEMIC TOXICITY
- Amendment :
- 51
- Comments :
- When used in the same fragrance compound within a specific QRA category, the sum total of and Methyl heptine carbonate (MHC, CAS number 111-12-6) and Methyl octine carbonate (MOC, CAS number 111-80-8) contributions must not exceed the maximum permitted level for MHC. At the same time, the contribution from MOC should always respect the maximum levels permitted as listed in the table above.
- Quantitative usage limits :
-
Cat.1 Cat.2 Cat.3 Cat.4 Cat.5 Cat.6 Cat.7 Cat.8 Cat.9 Cat.10 Cat.11 0,38 % 0,11 % 2,3 % 2,1 % 0,53 % 1,2 % 1,6 % 0,18 % 4,1 % 0,78 % 0,18 %
To learn more about IFRA's standards : https://ifrafragrance.org/safe-use/library
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