Buy Piperonal heliotropin Cas-120-57-0
Buy Piperonal heliotropin Cas-120-57-0
Piperonal, also known as heliotropin, 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. The methylenedioxyphenyl group is found in other fragrances. Buy Piperonal heliotropin Cas-120-57-0
Natural occurrence
Piperonal naturally occurs in various plants. Examples include dill, violet flowers, and black pepper.
Preparation
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.[5][6][7] Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.[8]
Reactions
Piperonal, like all aldehydes, can be reduced to its alcohol (piperonyl alcohol) or oxidized to give its acid (piperonylic acid).
Piperonal can be used in the synthesis of some pharmaceutical drugs including tadalafil,[9] L-DOPA,[10] and atrasentan.[11]
Fragrance
Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. For this reason it is commonly used in fragrances and artificial flavors.[5] The compound was named heliotropin 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).[12] Perfumers began to use the fragrance for the first time by the early 1880s.[13] It is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent’s character. Buy Piperonal heliotropin Cas-120-57-0
Piperonyl acetate is a synthetic cherry flavoring.[15]
Use in MDMA manufacture
Due to their role in the manufacture of MDMA, safrole, isosafrole, and piperonal are Category I precursors under regulation no. 273/2004 of the European Community.
Moreover, piperonal’s unique structure allows it to be employed in the production of pharmaceuticals and agrochemicals, showcasing its relevance in diverse fields. Researchers appreciate its role in organic synthesis, where it can be used as a building block for creating more complex compounds. With its multifaceted applications and appealing characteristics, piperonal crystals stand out as a valuable resource for professionals seeking to enhance their products or explore new chemical pathways. Buy Piperonal heliotropin Cas-120-57-0
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CAS Number: 120-57-0
Molecular Formula: C8H6O3
Structure Formula:
Piperonal BP EP USP CAS 120-57-0
Package: 25Kgs/Fiber Drum
Description:
Piperonal BP EP USP CAS 120-57-0, also known as heliotropin, is a chemical compound with the molecular formula C8H6O3. It is an organic compound that belongs to the family of aldehydes and is used in a wide range of applications, including in perfumes, fragrances, pharmaceuticals, and as a flavoring agent in food.
Cas Number: 120-57-0Buy Piperonal heliotropin Cas-120-57-0
Synonyms: Heliotropin, 1,3-Benzodioxol e-5-carboxaldehyde, 3,4-methylenedioxybenzaldehyde
Appearance: Piperonal BP EP USP CAS 120-57-0 is a white crystalline solid with a sweet and flowery odor.
Molecular formula: C8H6O3
Solubility: Piperonal BP EP USP CAS 120-57-0 is slightly soluble in water, but it dissolves readily in organic solvents, such as ethanol, methanol, and acetone.
Melting Point: Piperonal has a melting point of 37.5°C to 38.5°C.
Description: Piperonal is a synthetic compound that is typically produced by the oxidation of safrole. It is widely used in the fragrance industry as a fixative and as a flavoring agent in food. It is also used in the manufacture of pharmaceuticals and as an insecticide.
Density: The density of piperonal is 1.219 g/cm3 at 25°C.
Characteristics: Piperonal has a sweet and floral odor, which makes it suitable for use in perfumes and fragrances. It is also used in the food industry as a flavoring agent due to its faintly sweet taste. Piperonal is known for its insecticidal properties and is used as an insecticide to control the population of insects, such as fleas, ticks, and mites.
Applications: Piperonal is used in a variety of applications, including in perfumes and fragrances, as a flavoring agent in food, in the manufacture of pharmaceuticals, and as an insecticide. It is also used in the synthesis of other compounds, such as MDA, MDMA, and MDE.
Package transportation: Piperonal is typically packaged in sealed containers, such as glass or plastic bottles or drums, to prevent contamination and spills. It is transported by land, sea, or air, depending on the quantity, destination, and mode of transport.
Manufacture Procedures: Piperonal is typically produced by the oxidation of safrole, which is a component of many essential oils, such as sassafras oil. The oxidation is achieved by using oxidizing agents, such as potassium permanganate, sodium dichromate, or chromium trioxide. The resulting mixture is acidified and the piperonal is extracted by steam distillation. The piperonal is then purified by recrystallization to remove impurities.
Conclusion: Piperonal is a versatile chemical compound that is used in a wide range of applications, including in perfumes, fragrances, pharmaceuticals, and as a flavoring agent in food. It is known for its sweet, floral odor, faintly sweet taste, and insecticidal properties, which make it a valuable chemical in various industries. Piperonal is produced by the oxidation of safrole and is typically packaged in sealed containers for transportation.
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Documents
CAS Number
Product Name
IUPAC Name
Molecular Formula
Molecular Weight
InChI
InChI Key
SMILES
solubility
In water, 3.5X10+3 mg/L at 20 °C
Soluble in 500 parts water
Slightly soluble in water
Very soluble in ethanol; miscible with ethyl ether; soluble in acetone, chloroform
Slightly soluble in glycerol
3.5 mg/mL at 20 °C
slightly soluble in water; soluble in organic solvents, oils
freely soluble (in ethanol)
Synonyms
Canonical SMILES
Piperonal, also known as heliotropin, is an organic compound classified as an aromatic aldehyde. Its chemical structure is characterized by a benzodioxole framework with a formyl group at the 5-position, represented by the formula C₈H₆O₃. This compound is recognized for its pleasant floral aroma, reminiscent of cherry and vanilla, making it a popular ingredient in the fragrance and flavor industries. Piperonal is naturally found in various plants, including dill, vanilla, violet flowers, and black pepper .
Research on the mechanism of action of piperonal for its various biological effects is ongoing. Here are some potential areas of interest:
- Antioxidant activity: Piperonal might act as a free radical scavenger, protecting cells from oxidative damage [].
- Insulin signaling: Studies suggest it may upregulate insulin signaling molecules, potentially improving blood sugar control [].
- Antimicrobial activity: The mechanism behind this activity is not fully understood but might involve disrupting bacterial membranes [].
Antioxidant Properties:
Some scientific research suggests that piperonal might exhibit antioxidant properties. Antioxidants are compounds that help protect cells from damage caused by free radicals. Free radicals are unstable molecules that can contribute to the development of various health conditions.
Studies have observed that piperonal demonstrates free radical scavenging activity in cell cultures []. This indicates its potential role in mitigating oxidative stress, a condition associated with chronic diseases. However, further research is needed to determine the effectiveness and safety of piperonal for this purpose in living organisms.
Piperonal can undergo several chemical transformations typical of aldehydes:
- Reduction: It can be reduced to piperonyl alcohol.
- Oxidation: Piperonal can be oxidized to form piperonylic acid.
- Self-condensation: Like many aldehydes, it may participate in self-condensation reactions or polymerization processes when catalyzed by acids .
These reactions are significant for its applications in synthesizing other chemical compounds.
Piperonal exhibits various biological activities. Research indicates that it possesses antimicrobial properties and may have potential as a therapeutic agent. For instance, studies have shown that piperonal can inhibit the growth of certain bacteria and fungi. Additionally, its central nervous system depressant effects have been noted, leading to potential implications for its use in pharmacology .
Piperonal can be synthesized through several methods:
- Oxidative Cleavage of Isosafrole: This method involves the oxidative cleavage of isosafrole using reagents like chromic acid or through ozonolysis .
- Chemo-Enzymatic Methods: A recent study described a three-step chemo-enzymatic process that converts isosafrole into piperonal using lipase-mediated epoxidation followed by oxidation with manganese dioxide .
- Condensation Reactions: Piperonal can also be synthesized from catechol or 1,2-methylenedioxybenzene through condensation with glyoxylic acid, followed by oxidizing cleavage of the resultant product .
Piperonal finds extensive applications across various industries:
- Fragrance Industry: Due to its pleasant aroma, it is widely used in perfumes and scented products.
- Flavoring Agent: It serves as a flavor enhancer in food products, contributing cherry-like notes.
- Pharmaceuticals: Piperonal is utilized as an intermediate in the synthesis of pharmaceutical compounds such as tadalafil and L-DOPA .
Studies on piperonal’s interactions indicate potential effects on biological systems. For example, research has highlighted its interactions with neurotransmitter systems in the brain, suggesting possible anxiolytic effects. Additionally, piperonal’s role as a precursor in the synthesis of illicit drugs like MDMA raises concerns regarding its regulation and safety in certain contexts .
Piperonal shares structural similarities with several other aromatic aldehydes. Below is a comparison highlighting its uniqueness:
| Compound | Structure Type | Unique Features |
|---|---|---|
| Benzaldehyde | Simple aromatic aldehyde | Commonly used as a flavoring agent; less complex than piperonal. |
| Vanillin | Aromatic aldehyde | Known for its vanilla scent; used extensively in food and fragrances. |
| Safrole | Aromatic ether | Precursor to piperonal; has different biological properties and regulatory status. |
| Eugenol | Aromatic ether | Found in clove oil; has analgesic properties distinct from those of piperonal. |
Piperonal’s unique combination of aromatic properties and biological activities distinguishes it from these similar compounds, particularly in its applications within the fragrance industry and its synthesis pathways.
Physical Description
Liquid; Pellets or Large Crystals
Colorless lustrous solid; mp = 37 deg C; [Merck Index] White shining solid with a floral odor; Darkens to red-brown on light exposure; mp = 35.5-37 deg C; [Hawley] Colorless solid; mp = 36 deg C; [MSDSonline]
Solid
white or colourless crystals with a sweet, floral, spicy odou
Color/Form
White or colorless crystals
Turns brown on exposure to light
Forms white crystals (MP 37 °C)
XLogP3
Hydrogen Bond Acceptor Count
Exact Mass
Monoisotopic Mass
Boiling Point
263 °C
BP: 88 °C at 0.5 mm Hg
263.00 to 265.00 °C. @ 760.00 mm Hg
Heavy Atom Count
Taste
LogP
1.05
log Kow = 1.05
Odor
Floral odor
Sweet, flowery odor reminiscent of heliotrope
Sweet-floral, slightly spicey, heliotrope-like odo
Melting Point
37 °C
MP: 35.5-37 °C
UNII
GHS Hazard Statements
Reported as not meeting GHS hazard criteria by 339 of 1949 companies. For more detailed information, please visit ECHA C&L website;
Of the 8 notification(s) provided by 1610 of 1949 companies with hazard statement code(s):;
H317 (96.77%): May cause an allergic skin reaction [Warning Sensitization, Skin];
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Use and Manufacturing
Therapeutic Uses
/EXPL THER/ Background. Many families find regular checking of children’s heads for head louse infestation too onerous and would prefer to be able to prevent infestation by use of a topical application that deters lice from infesting the head. Identification in the laboratory of a repellent activity for piperonal provided the basis for developing a spray product to repel lice. Methods. A proof of principle field study in Dhaka, Bangladesh, compared the effect of using 2% piperonal spray with that of a placebo in 105 children and adults from three communities with infestation levels close to 100%. All participants were treated for infestation and subsequent incidence of reinfestation monitored daily by investigators. A second randomised, controlled, double blind, study in North London, UK, evaluated the effect of the product in normal use. One hundred and sixty-three children from schools with a high level (20-25%) of infestation were treated and confirmed louse free and randomly divided between 2% piperonal, a placebo spray, and a control group for up to 22 weeks. Parents applied the spray and monitored for infestation. Regular investigator visits confirmed the parental monitoring and replenished supplies of spray. Results. In Dhaka, over 18 days there were only 4 infestations in the piperonal group and 8 in the placebo group. This difference was not significant (p = 0.312). In North London, there were 41 cases of infestation over the course of the study. Although there were fewer infestations in the piperonal group, analysis of time to first infestation showed a no significant (p = 0.4368) difference between groups. Conclusion. Routine use of 2% piperonal spray in communities with a high prevalence of head louse infestation may provide some protection from infestation. However, the difference between use of the product and no active intervention was sufficiently small that regular checking for presence of lice is likely to be a more practical and cost effective approach to prevention of infestation.
/EXPL THER/ Piperonal, once used to kill lice in Australian hospitals, was acclaimed as an effective pediculicide (Corlette, 1925) by the standards of the day. It is unusual in also exhibiting a repellent action against lice, a property only recently realised. A new, easy to use, low-fragrance, pump action spray, which incorporates 2% piperonal, was tested in the laboratory using clothing lice in an arena test and was found to exhibit consistently high repellency after half an hour, dropping only slightly after 24 hours. A well known multi-purpose insect repellent, diethyltoluamide (DEET), was then tested against piperonal. A 2% solution of piperonal was found to be almost twice as effective as a 50% solution of DEET. In arena tests using lice with the tip segments of both antennae removed, no behavioral differences or statistically significant differences from a random distribution could be found between untreated and Rappell-treated areas. This strongly suggests that sense organ(s) on the tip of the antenna are necessary for detection of the repellent. Although there can be no strict correlation between results in the laboratory and potential efficacy in the field, materials such as insecticides found to be effective in the laboratory have been found to be equally effective in the field. Furthermore, what with the threat of resistance to head lice insecticides, ineffectual treatment and the lack of contact tracing, a repellent would be of obvious use in the control of head lice.
Vapor Pressure
0.01 [mmHg]
1X10-2 mm Hg at 25 °C (extrapolated)
Pictograms
Irritant
Other CAS
Metabolism Metabolites
In houseflies piperonal is metabolized to piperonylic acid which can be converted to a glycine conjugate or to an alanine conjugate or a glutamine conjugate. The alanine conjugate is further converted to a serine conjugate and the glutamine conjugate to a glutamate conjugate. /From table/
In rats piperonal is metabolized to piperonylic acid which is converted to glucuronide or to a glycine conjugate. /From table/
The beta-glucoside of piperonyl alcohol has also been found after injection of…piperonal into houseflies.
For more Metabolism/Metabolites (Complete) data for Piperonal (7 total), please visit the HSDB record page.
Wikipedia
Norethisterone_acetate
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Cosmetics -> Skin conditioning; Masking
Methods of Manufacturing
By the oxidation of isosafrole with potassium dichromate and sulfuric acid and subsequent steam distillation of piperonal.
Derivation: By oxidation of isosafrole.
The biotransformation of isosafrole by Cladosporium sphaerospermum yielded piperonal, which is a compound of great commercial importance in the flavor and fragrance industries. The experiments were performed in 500-mL conical flasks containing 100 mL of Czapek-modified medium in an orbital shaker with controlled agitation and temperature. Spores of C. sphaerospermum were used as inocula, and after 96 hr of incubation the substrate was added to the culture. Samples of 2 mL were withdrawn at 24-hr intervals and analyzed by gas chromatography, (GC) and/or GC/MS spectroscopy.
For more Methods of Manufacturing (Complete) data for Piperonal (8 total), please visit the HSDB record page.
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
All Other Chemical Product and Preparation Manufacturing
1,3-Benzodioxole-5-carboxaldehyde: ACTIVE
Storage Conditions
Keep in cool place protected from light.
Interactions
Stability Shelf Life
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Key Applications of Piperonal
Fragrance and Flavor Production
Piperonal is widely used in the perfume and flavor industry due to its distinctive floral, vanilla-like scent. It serves as an important ingredient in fine fragrances, flavorings, and aromatic formulations.
Pharmaceutical and Chemical Synthesis
In pharmaceutical manufacturing, piperonal is a valuable compound for synthesizing various drugs and active ingredients, providing a reliable building block in organic synthesis.
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