107-75-5 Usage
Description
Hydroxycitronellal 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.
Chemical Properties
Different sources of media describe the Chemical Properties of 107-75-5 differently. You can refer to the following data:
1. Hydroxycitronellal has a sweet, floral, lily-type odor
2. clear colourless liquid
3. This is a colorless,
slightly viscous liquid with a floral odor reminiscent of linden blossom and lily of
the valley. Commercially available “hydroxycitronellal” is either optically active
or racemic, depending on the starting material used. Hydroxydihydrocitronellal
prepared from (+)-citronellal, for example, has a specific relation α20
D +9 to +10°.
Hydroxydihydrocitronellal is relatively unstable toward acid and alkali and is,
therefore, sometimes converted into more alkali-resistant acetals, particularly its
dimethyl acetal.
Because of its fine, floral odor, hydroxydihydrocitronellal is used in large
quantities in many perfume compositions for creating linden blossom and lily of
the valley notes. It is also used in other blossom fragrances such as honeysuckle,
lily, and cyclamen.
Occurrence
Reported found in pepper
Uses
Different sources of media describe the Uses of 107-75-5 differently. You can refer to the following data:
1. Hydroxycitronellal 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).
2. 7-Hydroxycitronellal shows fungicide activity the strains of Candida tropicalis.
Preparation
The 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].
Definition
ChEBI: The tertiary alcohol arising from addition of water across the C2C double bond of citronellal.
Taste threshold values
Taste characteristics at 50 ppm: sweet, waxy, green, floral and melon notes.
Flammability and Explosibility
Notclassified
Trade name
Laurinal? (Takasago).
Contact allergens
Hydroxycitronellal is a classical fragrance allergen, found
in many products. It is contained in “fragrance mix.” It
has to be listed by name in the cosmetics of the EU.
Safety Profile
A skin irritant.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALDEHYDES.
Synthesis
By hydration of natural citronellal obtained from Java citronella or from Eucalyptus citriodora; β-pinene is converted
to myrcene, which on hydration may yield either linalool or 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.
Check Digit Verification of cas no
The CAS Registry Mumber 107-75-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 107-75:
(5*1)+(4*0)+(3*7)+(2*7)+(1*5)=45
45 % 10 = 5
So 107-75-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3/t9-/m0/s1
107-75-5Relevant articles and documents
Efficient green synthesis method of hydroxycitronellal
-
Paragraph 0013; 0027; 0030-0032; 0035; 0038-0040; 0041; ..., (2021/06/26)
The invention discloses an efficient green synthesis method of hydroxycitronellal. The method comprises the following steps: adding POL-PPh3, PdCl2 and anhydrous THF into a sealed container according to a mass ratio of (100: 5)-(10: 1), reacting at 25-35 DEG C overnight, filtering, removing filtrate, washing filter residues twice with ethyl acetate and ethanol respectively, and collecting solids to obtain a POL-PPh3-coated PdCl2 solid catalyst; taking 1 part by mass of a POL-PPh3-coated PdCl2 catalyst, 10-35 parts by mass of citronellal, 7-20 parts by mass of water and 500-800 parts by mass of toluene, uniformly stirring, and reacting at 180-200 DEG C for 10-24 hours to obtain a reaction solution; after the reaction liquid is cooled, filtering and separating the solid catalyst, fractionating the reaction liquid, and collecting a distillate at 257 DEG C, thereby obtaining the hydroxycitronellal. According to the method, citronellal and water are directly synthesized into hydroxycitronellal in one step under the catalysis of POL-PPh3-coated PdCl2, the method has the advantages of being environmentally friendly, low in price, high in catalytic efficiency, high in yield, mild in reaction condition, high in production efficiency, simple in process, non-toxic, harmless, free of emission of three wastes and the like, and a good foundation is laid for large-scale production of hydroxycitronellal.
Preparation method of citronellal hydrate
-
Paragraph 0065; 0069; 0070; 0078; 0086; 0094; 0102, (2018/04/03)
The invention relates to a preparation method of citronellal hydrate. The method comprises the steps of citronellal oxazolidine derivative preparation, solid acid catalytic reaction, aftertreatment and the like. The purity of a citronellal hydrate product prepared by using the method provided by the invention reaches 95% or above. The method provided by the invention has the characteristics that asolid acidification catalyst is easily separated from a reactant, can be repeatedly used and cannot corrode a reactor, catalytic public hazards are reduced, and the wastewater amount is greatly reduced. By using the method provided by the invention, an environment-friendly synthesis process route is achieved.
NEW APPROACHES TO THE SYNTHESIS OF 7-ALKOXY- AND 7-HYDROXY-6,7-DIHYDROCITRALS
Erman, M. B.,Golovacheva, E. V.,Gulyi, S. E.,Zasetskii, D. L.,Shutikova, L. A.,et al.
, p. 219 - 221 (2007/10/02)
7-Alkoxy-6,7-dihydrocitrals were obtained by the rearrangement of ethynylcarbinols in the presence of polyvanadioorganosiloxane. 7-Hydroxy-6,7-dihydrocitral was obtained by the hydration of citral 1,3-disulfonate in an acidic medium followed by alkaline decomposition of the hydration product.