| Record Information |
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| Version | 2.0 |
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| Created at | 2012-09-11 18:20:11 UTC |
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| Updated at | 2024-09-15 13:03:34 UTC |
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| NP-MRD ID | NP0000030 |
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| Natural Product DOI | https://doi.org/10.57994/0470 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Safrole |
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| Description | 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. Safrole is found in anise and nutmeg. Banned by FDA for use in food. Safrole is 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. Safrole is 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 rat, mouse and human (PMID:6719936 ). The Ocotea cymbarum oil made of the Ocotea pretiosa, 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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| Structure | 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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| Synonyms | | Value | 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 |
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| Chemical Formula | C10H10O2 |
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| Average Mass | 162.1852 Da |
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| Monoisotopic Mass | 162.06808 Da |
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| IUPAC Name | 5-(prop-2-en-1-yl)-2H-1,3-benzodioxole |
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| Traditional Name | sassafras |
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| CAS Registry Number | 94-59-7 |
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| SMILES | C=CCC1=CC2=C(OCO2)C=C1 |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 500.33, CDCl3, simulated) | Not Available | Not Available | Not Available | 2024-05-11 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 11.2 °C | Not Available | | Boiling Point | 232–234 °C | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Ioannides C, Lum PY, Parke DV: Cytochrome P-448 and the activation of toxic chemicals and carcinogens. Xenobiotica. 1984 Jan-Feb;14(1-2):119-37. [PubMed:6719936 ]
- Hung SL, Chen YL, Chen YT: Effects of safrole on the defensive functions of human neutrophils. J Periodontal Res. 2003 Apr;38(2):130-4. [PubMed:12608906 ]
- Zhao J, Miao J, Zhao B, Zhang S, Yin D: Safrole oxide inhibits angiogenesis by inducing apoptosis. Vascul Pharmacol. 2005 Jun;43(1):69-74. [PubMed:15936989 ]
- Benedetti MS, Malnoe A, Broillet AL: Absorption, metabolism and excretion of safrole in the rat and man. Toxicology. 1977 Feb;7(1):69-83. doi: 10.1016/0300-483x(77)90039-7. [PubMed:14422 ]
- Authors unspecified: Safrole. Rep Carcinog. 2002;10:213-4. [PubMed:15334724 ]
- Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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