Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:46 UTC |
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Update date | 2019-11-26 03:05:14 UTC |
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Primary ID | FDB011672 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Safrole |
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Description | Occurs in nutmeg. Banned by FDA for use in food. Formerly used as a food flavour
It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy."); Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. A major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in the rat, mouse and man. (PMID: 6719936); Safrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. The Ocotea cymbarum[verification needed] oil made of the Ocotea pretiosa[verification needed], a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma. |
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CAS Number | 94-59-7 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Methylenedioxy-4-allylbenzene | ChEBI | 1-Allyl-3,4-methylenedioxybenzene | ChEBI | 3,4-(Methylenedioxy)allylbenzene | ChEBI | 3-(3,4-Methylenedioxyphenyl)prop-1-ene | ChEBI | 4-Allyl-1,2-methylenedioxybenzene | ChEBI | 4-Allylpyrocatechol formaldehyde acetal | ChEBI | 5-(2-Propenyl)-1,3-benzodioxole | ChEBI | 5-Allyl-benzo[1,3]dioxole | ChEBI | Allylcatechol methylene ether | ChEBI | m-Allylpyrocatechin methylene ether | ChEBI | Safrol | ChEBI | Shikimol | ChEBI | Shikimole | ChEBI | (1,2-(Methylenedioxy)-4-allyl)benzene | HMDB | (Allyldioxy)benzene methylene ether | HMDB | (e)5-1-Propenyl]-1,3-benzodioxole | HMDB | 1, 2-(Methylenedioxy)-4-allylbenzene | HMDB | 1,2-(Methylenedioxy)-4-propenylbenzene | HMDB | 1,2-Methylenedioxy-4-allyl-benzene | HMDB | 1-Allyl,3,4-methylenedioxy benzene | HMDB | 3, 4-(Methylenedioxy)allylbenzene | HMDB | 3,4-(Methylenedioxy)-1-propenylbenzene | HMDB | 3,4-Methylenedioxy-allybenzene | HMDB | 3,4-Methylenedioxyallylbenzene | HMDB | 4-Allyl-1, 2-(methylenedioxy)benzene | HMDB | 4-Allyl-1,2-(methylenedioxy)benzene, 8ci | HMDB | 4-Allylpyrocatechol | HMDB | 4-Propenyl-1,2-methylenedioxybenzene | HMDB | 4-Propenylcatechol methylene ether | HMDB | 5-(1-Propenyl)-1,3-benzodioxole | HMDB | 5-(2-Propenyl)-1,3-benzodioxole, 9ci | HMDB | 5-Allyl-1,3-benzodioxolerlet DS base | HMDB | 5-Prop-2-enyl-1,3-benzodioxole | HMDB | 6-(1-Propenyl)-1,3-benzodioxole | HMDB | Allyldioxybenzene methylene ether | HMDB | Allylpyrocatechol methylene ether | HMDB | Isosafrol | HMDB | Isosafrole | HMDB | Izosafrol | HMDB | Shikomol | HMDB | 4 Allyl 1,2 methylenedioxybenzene | MeSH | 4-Allyl-1,2-methylenedioxybenzenes | MeSH | Safroles | MeSH | Shikimols | MeSH | Safrols | MeSH | 4-Allyl-1,2-(methylenedioxy)benzene, 8CI | db_source | 5-(2-Propenyl)-1,3-benzodioxole, 9CI | db_source | 5-Allyl-1,3-benzodioxolerlet DS Base | biospider |
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Predicted Properties | |
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Chemical Formula | C10H10O2 |
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IUPAC name | 5-(prop-2-en-1-yl)-2H-1,3-benzodioxole |
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InChI Identifier | InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2 |
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InChI Key | ZMQAAUBTXCXRIC-UHFFFAOYSA-N |
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Isomeric SMILES | C=CCC1=CC2=C(OCO2)C=C1 |
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Average Molecular Weight | 162.1852 |
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Monoisotopic Molecular Weight | 162.068079564 |
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Classification |
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Description | Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzodioxoles |
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Sub Class | Not Available |
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Direct Parent | Benzodioxoles |
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Alternative Parents | |
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Substituents | - Benzodioxole
- Benzenoid
- Oxacycle
- Acetal
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Environmental role: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.06%; H 6.21%; O 19.73% | DFC |
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Melting Point | Fp 11.2° | DFC |
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Boiling Point | Bp6 104-105° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | n20D 1.5383 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0ik9-4900000000-9558c12b4c5a01a27490 | 2014-09-20 | View Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-3900000000-27e98ee529004a2d8b66 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-6900000000-54b4c1509456711936df | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-03di-6900000000-87b7efd770862a8f97a5 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-5900000000-0e7164aea8e5fa73ab55 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-03di-0900000000-cae3268c72651c72100c | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-3900000000-27e98ee529004a2d8b66 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-6900000000-54b4c1509456711936df | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-03di-6900000000-87b7efd770862a8f97a5 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-0ik9-5900000000-0e7164aea8e5fa73ab55 | Spectrum | GC-MS | Safrole, non-derivatized, GC-MS Spectrum | splash10-03di-0900000000-cae3268c72651c72100c | Spectrum | Predicted GC-MS | Safrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01sa-2900000000-390702c1e607859e4700 | Spectrum | Predicted GC-MS | Safrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-ce90b24b2ef83a609261 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-1900000000-cb602c608751e483efce | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udl-9600000000-85407378b64267759f6d | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-f5650e9b49b023a3cfd2 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-9dbd3903283425175546 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02ti-5900000000-4204c0caaf5bb9b5d258 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-9b0c6d7bc981d77b1927 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03k9-0900000000-01530378eccaf5c845f0 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvr-9400000000-d251b0867c3f55c2e90e | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-4d3d221c51bdf4e740a2 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-3a92a79dc10e1183839f | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01ot-7900000000-1024f7dba32bfc58ce37 | 2021-09-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 13848731 |
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ChEMBL ID | CHEMBL242273 |
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KEGG Compound ID | C10490 |
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Pubchem Compound ID | 5144 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB33591 |
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CRC / DFC (Dictionary of Food Compounds) ID | GXV45-I:GXV45-I |
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EAFUS ID | 3354 |
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Dr. Duke ID | SAFROLE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002771 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 94-59-7 |
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GoodScent ID | rw1010791 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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anesthetic | | | DUKE | anti aggregant | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti convulsant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | carminative | | | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | central nervous system stimulant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | controlled | | | DUKE | cytochrome-p450 inducer | | | DUKE | cytochrome-p488 inducer | | | DUKE | DNA-binder | | | DUKE | hepatocarcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | hepatoregenerative | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | hepatotoxic | 50908 | A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. | DUKE | hypothermic | | | DUKE | irritant | | | DUKE | mutagenic | | | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | DUKE | pediculicide | 38706 | Substance used to treat lice (genus Pediculus) infestation. | DUKE | perfumery | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | psychoactive | 35471 | A loosely defined grouping of drugs that have effects on psychological function. | DUKE | tremorigenic | | | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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spice |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| sweet |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| warm |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| floral |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sassafrass |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| anise |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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