# Piperonal
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> Markdown URL: https://mediated.wiki/source/Piperonal.md
> Source: https://en.wikipedia.org/wiki/Piperonal
> Source revision: 1346789353
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 394986228
| Name = Piperonal
| ImageFile = Piperonal structure.png
| ImageClass = skin-invert
| ImageName =
| PIN = 2''H''-1,3-Benzodioxole-5-carbaldehyde
| OtherNames= Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde;
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KE109YAK00
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8240
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 271663
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SATCULPHIDQDRE-UHFFFAOYSA-N
| SMILES1 = c1cc2c(cc1C=O)OCO2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 120-57-0
| Beilstein = 131691
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13859497
| EC_number = 204-409-7
| Gmelin = 4186
| KEGG = C10812
| PubChem = 8438
| SMILES = O=Cc1ccc2OCOc2c1
}}
|Section2={{Chembox Properties
| C=8 | H=6 | O=3
| Appearance = Colorless crystals[{{Merck12th}}]
| Density = 1.337 g/cm3
| MeltingPtC = 37
| MeltingPt_ref = [
| BoilingPtC = 263
| BoilingPt_ref = ][
| Solubility = Soluble in 500 parts][
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|321|333+313|363|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
| LD50 = 2700 mg/kg (orally in rats)][ }}
|Section4={{Chembox Legal status
| legal_AU =
| legal_BR = D1
| legal_BR_comment = ][{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[Diário Oficial da União](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) |language=pt-BR |publication-date=2023-04-04}}]
| legal_EU = category 1 precursor
| legal_EU_comment = [{{CELEX|32004R0273|text=Regulation (EC) No 273/2004 of the European Parliament and of the Council of 11 February 2004 on drug precursors}}]
| legal_US = List I
| legal_US_comment = [{{cite web |title=List I and II Regulated Chemicals - Alphabetical Order |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/f_chemlist_alpha.pdf?page=2 |website=www.deadiversion.usdoj.gov |publisher=DEA Diversion - US DOJ |access-date=21 September 2025 |page=2 |date=19 September 2025}}]
| legal_UK =
| legal_UN =
}}
}}
'''Piperonal''', also known as '''heliotropin''', is an [organic compound](/source/organic_compound) which is commonly found in fragrances and flavors. The molecule is structurally related to other [aromatic](/source/aromatic) [aldehyde](/source/aldehyde)s such as [benzaldehyde](/source/benzaldehyde) and [vanillin](/source/vanillin). The methylenedioxyphenyl group is found in other fragrances.[{{cite book|last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |date=2016 |pages=1–45 |doi=10.1002/14356007.t11_t02 |isbn=978-3-527-30673-2 }}]
== Natural occurrence ==
Piperonal naturally occurs in various plants. Examples include [dill](/source/dill), [violet flowers](/source/Viola_odorata), and [black pepper](/source/black_pepper).
==Preparation==
Piperonal can be prepared by the oxidative cleavage of [isosafrole](/source/isosafrole) or by using a multistep sequence from [catechol](/source/catechol) or [1,2-methylenedioxybenzene](/source/1%2C3-Benzodioxole). Synthesis from the latter chemical is accomplished through a [condensation reaction](/source/condensation_reaction) with [glyoxylic acid](/source/glyoxylic_acid) followed by [cleaving](/source/Bond_cleavage) the resulting [α-hydroxy acid](/source/Alpha_hydroxy_acid) with an [oxidizing agent](/source/oxidizing_agent).[{{cite journal|author1=Fatiadi, Alexander |author2=Schaffer, Robert |name-list-style=amp |title=An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)|journal=Journal of Research of the National Bureau of Standards Section A|year=1974|volume=78A|issue=3|pages=411–412|doi=10.6028/jres.078A.024|pmid=32189791 |pmc=6742820 |doi-access=free}}][{{cite journal|last1=Nwaukwa|first1=Stephen|last2=Keehn|first2=Philip|title=Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite [Ca(OCl)2]|journal=Tetrahedron Letters|date=1982|volume=23|issue=31|pages=3135–3138|doi=10.1016/S0040-4039(00)88578-0}}] Synthesis from catechol requires an additional step, [Williamson ether synthesis](/source/Williamson_ether_synthesis) using [dichloromethane](/source/dichloromethane).[{{cite journal|author1=Bonthrone, W. |author2=Cornforth, J. |name-list-style=amp |title=The methylenation of catechols|journal=Journal of the Chemical Society|issue=9 |year=1969|pages=1202–1204|doi=10.1039/J39690001202}}]
==Reactions==
Piperonal, like all [aldehyde](/source/aldehyde)s, can be [reduced](/source/Carbonyl_reduction) to its [alcohol](/source/Alcohol_(chemistry)) ([piperonyl alcohol](/source/piperonyl_alcohol)) or oxidized to give its [acid](/source/carboxylic_acid) ([piperonylic acid](/source/piperonylic_acid)).
Piperonal can be used in the synthesis of some pharmaceutical drugs including [tadalafil](/source/tadalafil),[{{cite journal|author1=Gilla, G.|author2=Anumula, R.R.|author3=Aalla, S.|author4=Vurimidi, H.|author5=Ghanta, M.R.|name-list-style=amp|title=Synthesis and characterization of related substances and metabolite of tadalafil, a PDE-5 inhibitor|journal=Organic Communications|year=2013|volume=6|issue=1|pages=12–22|url=http://www.acgpubs.org/OC/2013/Volume%206/Issue%201/2-OC-1204-256.pdf|access-date=2015-01-21|archive-date=2018-10-24|archive-url=https://web.archive.org/web/20181024112519/http://www.acgpubs.org/OC/2013/Volume%206/Issue%201/2-OC-1204-256.pdf|url-status=live}}] [L-DOPA](/source/L-DOPA),[{{cite journal | doi = 10.1248/cpb.10.680| title = Studies on Optically Active Amino Acids. I. Preparation of 3-(3, 4-Methylenedioxyphenyl)-D-, and -L-alanine| journal = Chemical & Pharmaceutical Bulletin| volume = 10| issue = 8| pages = 680–688| year = 1962| last1 = Yamada| first1 = Shun-Ichi| last2 = Fujii| first2 = Tozo| last3 = Shioiri| first3 = Takayuki| pmid = 14002245| doi-access = free}}] and [atrasentan](/source/atrasentan).[{{cite journal|last1=Winn|first1=Martin|last2=von Geldern|first2=Thomas W.|last3=Opgenorth|first3=Terry J.|last4=Jae|first4=Hwan-Soo|last5=Tasker|first5=Andrew S.|last6=Boyd|first6=Steven A.|last7=Kester|first7=Jeffrey A.|last8=Mantei|first8=Robert A.|last9=Bal|first9=Radhika|last10=Sorensen|first10=Bryan K.|last11=Wu-Wong|first11=Jinshyun R.|last12=Chiou|first12=William J.|last13=Dixon|first13=Douglas B.|last14=Novosad|first14=Eugene I.|last15=Hernandez|first15=Lisa|last16=Marsh|first16=Kennan C.|title=2,4-Diarylpyrrolidine-3-carboxylic AcidsPotent ETASelective Endothelin Receptor Antagonists. 1. Discovery of A-127722|journal=Journal of Medicinal Chemistry|volume=39|issue=5|year=1996|pages=1039–1048|issn=0022-2623|doi=10.1021/jm9505369|pmid=8676339}}]
== Fragrance ==
Piperonal has a floral odor which is commonly described as being similar to that of vanillin or [cherry](/source/cherry). For this reason it is commonly used in fragrances and [artificial flavors](/source/Flavoring).[{{Cite web|url=http://www.bojensen.net/EssentialOilsEng/EssentialOils13A/EssentialOils13A.htm|title=Essential oils|access-date=2012-09-02|archive-date=2019-12-23|archive-url=https://web.archive.org/web/20191223140607/http://www.bojensen.net/EssentialOilsEng/EssentialOils13A/EssentialOils13A.htm|url-status=live}}] Perfumers began to use the fragrance for the first time by the early 1880s.[[https://books.google.com/books?id=_wGaNRoHWI0C&dq=1869+fittig+and+mielk&pg=PA107 The Force of Fashion in Politics and Society]: Global Perspectives from Early Modern to Contemporary Times By Beverly Lemire {{ISBN|9781409404927}}] It is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character.[{{cite web |title=heliotropin|url=https://scentsandflavors.com/database/9dbb4f8d-d5e7-4f34-aa9c-1681004947d7|website=Scents and Flavors |publisher=Scents and Flavors |access-date=3 April 2026}}]
[Piperonyl acetate](/source/Piperonyl_acetate) is a synthetic cherry flavoring.[Fenaroli's Handbook of Flavor Ingredients.]
== Use in MDMA manufacture ==
Due to their role in the manufacture of [MDMA](/source/MDMA), [safrole](/source/safrole), [isosafrole](/source/isosafrole), and piperonal are Category I precursors under regulation no. 273/2004 of the [European Community](/source/European_Community).[
== References ==
{{reflist}}
== External links ==
{{EB1911 poster|Piperonal}}
Category:Benzaldehydes
Category:Benzodioxoles
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Adapted from the Wikipedia article [Piperonal](https://en.wikipedia.org/wiki/Piperonal) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Piperonal?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.
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