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CAS NUMBER: 120-57-0
EC NUMBER: 204-409-7
MOLECULAR FORMULA: C8H6O3
MOLECULAR WEIGHT: 150.13
Piperonal is an organic compound which is commonly found in fragrances and flavors.
The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
Piperonal naturally occurs in various plants.
Examples include dill, vanilla, violet flowers, and black pepper.
Piperonal can be prepared by the oxidative cleavage of isosafrole or by using a multistep sequence from catechol or 1,2-methylenedioxybenzene.
Synthesis from the latter chemical is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent.
Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.
Piperonal, like all aldehydes, can be reduced to Piperonals alcohol (piperonyl alcohol) or oxidized to give its acid.
Piperonal can be used in the synthesis of some pharmaceutical drugs including tadalafil.
Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry.
For this reason Piperonal is commonly used in fragrances and artificial flavors.
The compound was named Piperonal after the 'cherry pie' notes found in the heliotrope flower's fragrance (even though the chemical is not present in the flower's true aroma).
Perfumers began to use the fragrance for the first time by the early 1880s.
Piperonal is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character.
Piperonyl acetate is a synthetic cherry flavoring.
Piperonal is an arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.
Piperonal has a role as a plant metabolite, a fragrance and an insect repellent.
Piperonal is a member of benzodioxoles and an arenecarbaldehyde.
Piperonal is a natural product found in Achillea ptarmica, Piper nigrum, and other organisms with data available.
Piperonal, also known as piperonyl aldehyde, belongs to the class of organic compounds known as benzodioxoles.
These are organic compounds containing a benzene ring fused to either isomers of dioxole.
Piperonal is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
Based on a literature review a significant number of articles have been published on 3,4-Methylenedioxybenzaldehyde.
Piperonal belongs to the class of organic compounds known as benzodioxoles.
These are organic compounds containing a benzene ring fused to either isomers of dioxole.
Piperonal is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
Piperonal is an aldehyde.
Piperonals are frequently involved in self-condensation or polymerization reactions.
These reactions are exothermic; they are often catalyzed by acid.
Piperonals are readily oxidized to give carboxylic acids.
Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents.
Piperonals can react with air to give first peroxo acids, and ultimately carboxylic acids.
These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).
The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.
Piperonal is sensitive to light.
Piperonal may react with oxidizing materials.
Piperonal is naturally found in various plants,including dill, vanilla, violet flowers, and black pepper,etc.
Piperonal occurs naturally in a variety of plants.
Examples include dill, vanilla, violet flowers, and black pepper.
Piperonal can be prepared by oxidative cleavage of isosafrole or using a multistep sequence with catechol or 1,2-methylenedioxybenzene.
Piperonal is achieved through a condensation reaction with glyoxylic acid followed by cleavage of the resulting α-hydroxy acid with an oxidizing agent.
Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.
Piperonal has a floral odor, commonly described as being similar to vanillin or cherry.
For this reason, Piperonal is widely used in fragrances and artificial flavors.
Piperonal was first used in perfumery in the early 1880s.
Piperonal is often used to add vanilla or almond nuances, often adding balsamic, powdery and floral qualities to the character of a fragrance.
Piperonal, also known as Piperonal, is an organic compound with common odors and flavors.
The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
As well as Piperonal and 3,4-methylenedioxybenzaldehyde.
Colorless or white crystals with heliotrope-like odor.
Piperonals melting point is 37°C, Boiling point is 144 (14 mmHg)°C.
Small amounts are found in floral essential oil such as Falseacacia.
Piperonal is produced industrially by the oxidation of isosafrol. Heliotrope formula is important as raw material for Perfume.
Widely used for general cosmetics, soap fragrance.
Piperonal is an intermediate used in the synthesis of DL-threo-Droxidopa-d3 (D689953), which is an isotope labelled compound of DL-threo-Droxidopa (D689950), a synthetic amino acid precursor of Norepinephrine.
Piperonal is the deuterated form of Piperonal (P490050), which is an impurity of Tadalafil.
Piperonal is a simple aromatic aldehyde compound with a characteristic cherry-like aroma and has been widely used in the flavor and fragrance industries.
Despite piperonal being an important aroma in black pepper (Piper nigrum), its biosynthesis remains unknown.
Piperonal is found in the essence of the locust bean plant.
Piperonal is prepared in the industry by the oxidation of isosafrol.
Piperonal forms white crystals that melt at 37°C.
Piperonal boils at 263°C. Slightly soluble in water, very soluble in alcohol and ether.
Bamboo is the main fragrance ingredient; It is mostly used in perfumery and sometimes as an antipyretic.
Piperonal, also known as Piperonal, is an organic compound which is commonly found in fragrances and flavors.
Piperonal is structurally related to other aromatic aldehydes.
Piperonal is an aromatic aldehyde that comes as transparent crystals, C8H6O3, and has a floral odor.
Piperonal can be obtained by oxidation of piperonyl alcohol.
Piperonal is also a minor natural component of the extract of vanilla.
Piperonal may be used in the synthesis of 3,4-methylenedioxyamphetamine (MDA).
In one synthetic path, nitroethane in a glacial acetic acid solution with an ammonium acetate catalyst yields a substituted nitrostyrene via a condensation reaction.
This intermediate can then be reduced in the presence of a strong reducing agent such as lithium aluminum hydride (LiAlH4) to yield MDA.
Reported found in the essential oils of Robinia pseudo-acacia and Eryngium poterium; in the oils of Spirea ulmaria and of leaves of Doryphora sassafras; also reported found in Tahitian and Bourbon vanilla, camphor wood oil, violet flowers concrete and absolute, burley tobacco, rabbiteye blueberry, melon, pepper, cooked chicken, sherry and dill.
Piperonyl aldehyde is an aldehyde.
Piperonals are exothermic; they are often catalyzed by acid.
Piperonals are readily oxidized to give carboxylic acids.
Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents.
Piperonals can react with air to give first peroxo acids, and ultimately carboxylic acids.
These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).
The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.
Piperonal is sensitive to light.
Piperonal may react with oxidizing materials.
By the oxidation of isosafrole with potassium dichromate and sulfuric acid and subsequent steam distillation of piperonal.
Piperonal has a sweet, flowery odor reminiscent of heliotrope and a bittersweet taste.
USES:
-fragrance
-perfuming agents
-skin conditioning
SPECIFICATIONS:
-Molecular Weight: 150.13
-Assay/Purity: 99-100
-Flash Point: 212°F (100°C)
-Boiling Point: 263°C
-Shelf Life: 36 MONTHS
PREPARATION:
Piperonal is produced by two main routes:
From isosafrole: For many years, oxidative cleavage of isosafrole was the only route applicable on an industrial scale.
Isosafrole is obtained by isomerization from safrole, which can be isolated from (Chinese) sassafras oil.
Examples of oxidants that give good yields of Piperonal are chromium(VI) salts, oxygen, and ozone.
This method is still used currently, but the destructive exploitation of sassafras trees in Southeast Asia has led to a strong decline in the availability of sassafras oil and thus of safrole/isosafrole.
From catechol: Several routes have recently been developed for the synthesis of Piperonal from catechol.
In one such route, catechol is converted into 3,4-dihydroxymandelic acid with glyoxylic acid in an alkaline medium in the presence of aluminum oxide.
Dihydroxymandelic acid is oxidized to the corresponding keto acid, which is decarboxylated to 3,4-dihydroxybenzaldehyde.
The latter product is converted into Piperonal, for example, by reactionwith methylene chloride in the presence of quaternary ammonium salts.
In another route, catechol is first reacted with methylene chloride and converted into 1,2-methylenedioxybenzene.
Reaction with glyoxylic acid in strongly acidic media yields 3,4-methylenedioxymandelic acid.
Subsequent oxidation and decarboxylation with nitric acid afford Piperonal.
Alternative routes that start from 1,2-methylenedioxybenzene and use piperonyl chloride as intermediate have been described.
CHARACTERISTICS:
-Appearance at 20°C: Crystalline solid
-Color: White (tends to yellow by heating)
-Odor: Sweet, floral
-Taste: Bittersweet
-Density at: 20°C (G/ML)) 0,000 - 0,000
-Refractive index: ND20 0,0000 - 0,0000
-Flashpoint: (°C) 120
-Solubility: 1 g in 4 ml ethanol 70º
-Assay: (% GC) > 99
PROPERTIES:
-vapor pressure: 1 mmHg ( 87 °C)
-Quality Level: 100
-assay: 99%
-form: solid
-bp: 264 °C (lit.)
-mp: 35-39 °C (lit.)
-SMILES string: [H]C(=O)c1ccc2OCOc2c1
-InChI: 1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
-InChI key:SATCULPHIDQDRE-UHFFFAOYSA-N
STORAGE:
Recommended storage temperature at 25ºc.
Keep in tightly closed container in a cool and dry place, protected from light.
When stored for more than 24 months, quality should be checked before use.
We believe the above information to be correct but we do not present it as all inclusive and as such should be used as a guide.
SYNONYM:
120-57-0
Piperonyl aldehyde
Piperonale
1,3-Benzodioxole-5-carbaldehyde
Piperonal
Piperonaldehyde
3,4-Methylenedioxybenzaldehyde
1,3-Benzodioxole-5-carboxaldehyde
Piperonylaldehyde
Geliotropin
3,4-(Methylenedioxy)benzaldehyde
5-Formyl-1,3-benzodioxole
Protocatechuic aldehyde methylene ether
3,4-Dihydroxybenzaldehyde methylene ketal
3,4-Bis(methylenedioxy)benzaldehyde
Dioxymethylene-protocatechuic aldehyde
3,4-Dimethylenedioxybenzaldehyde
Benzo[D][1,3]Dioxole-5-Carbaldehyde
benzo[1,3]dioxole-5-carbaldehyde
3,4-Methylene-dihydroxybenzaldehyde
Dioxymethylene protocatechuic aldehyde
UNII-KE109YAK00
2H-1,3-Benzodioxole-5-Carbaldehyde
NSC 26826
Benzaldehyde, 3,4-(methylenedioxy)-
CHEBI:8240
IUPAC NAME:
1,3-benzodioxole-5-carbaldehyde
1,3-Benzodioxole-5-carbaldehyde
1,3-benzodioxole-5-carbaldehyde
1,3-Benzodioxole-5-carboxaldehyde
2H-1,3-benzodioxole-5-carbaldehyde
3,4-Dihydroxybenzaldehyde methylene ketal
Benzo[d][1,3]dioxole-5-carbaldehyde
Piperonal
Piperonal
piperonal
Piperonal
