7470-44-2

Usage

Uses

Used in Pharmaceutical Industry:
Safrole oxide is used as a potential medicinal compound for its anti-inflammatory and anti-cancer activities. Preclinical studies have reported its effectiveness in modulating various biological pathways and exhibiting inhibitory effects on tumor growth and progression.
Used in Perfumery Industry:
Safrole oxide is used as a fragrance ingredient in perfumery due to its unique scent. Its aromatic properties make it a valuable component in the creation of various fragrances and scented products.
However, it is important to note that the use and production of safrole oxide are closely monitored and restricted in many parts of the world due to its association with the production of the illegal drug MDMA (ecstasy).

InChI:InChI=1/C10H10O3/c1-2-9-10(13-6-12-9)4-7(1)3-8-5-11-8/h1-2,4,8H,3,5-6H2

Upstream product

• 186581-53-3 diazomethane 
• 120-57-0 piperonal 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 106-89-8 epichlorohydrin 
• 60-29-7 diethyl ether 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 
• 4212-43-5 perpropionic acid 

Downstream Products

• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 6974-61-4 β-oxy-α-(3',4'-methylenedioxyphenyl)propane 
• 61051-19-2 5-bromo-4-(3-bromo-2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 74575-44-3 6-methyl-5H-[1,3]dioxolo[4,5-f]indole 
• 78757-01-4 5-nitro-4-(2-oxopropyl)-1,2-methylenedioxybenzene 
• 82341-83-1 5-nitro-4-(2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 82341-90-0 5-bromo-4-(3-cyano-2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 82341-87-5 4-(3-methoxycarbonyl-2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 82341-85-3 ethyl 3-(3,4-methylenedioxyphenyl)-4-oxopentanoate 
• 82341-92-2 4-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-hydroxy-butyric acid 
• 82341-91-1 5-bromo-4-(3-carbamoyl-2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 82341-86-4 5-nitro-4-(3-methoxycarbonyl-2-hydroxypropyl)-1,2-methylenedioxybenzene 
• 82341-88-6 4-(6-Nitro-benzo[1,3]dioxol-5-yl)-3-oxo-butyric acid methyl ester 
• 82341-84-2 5-nitro-4-(2-oxo-1-carboxymethylpropyl)-1,2-methylenedioxybenzene ethyl ester 

Relevant academic research and scientific papers

Safrole oxide induces neuronal apoptosis through inhibition of integrin β4/SOD activity and elevation of ROS/NADPH oxidase activity

Neuronal apoptosis is a very important event in the development of the central nervous system (CNS), but the underlying mechanisms remain to be elucidated. We have previously shown that safrole oxide, a small molecule, induces integrin β4 expression and promotes apoptosis in vascular endothelial cells. In this study, the effects of safrole oxide on cell growth and apoptosis have been examined in primary cultures of mouse neurons. Safrole oxide was found to significantly inhibit neuronal cell growth and to induce apoptosis. The inhibitory and apoptotic activities of safrole oxide followed a dose- and time-dependent manner. Interestingly, the expression of integrin β4 was significantly inhibited with safrole oxide treatment. Furthermore, safrole oxide dramatically increases the level of intracellular reactive oxygen species (ROS) and the activity of NADPH oxidase. Moreover, manganese-dependent superoxide dismutase (MnSOD) activity was decreased significantly with safrole oxide treatment. Our study thus demonstrates that safrole oxide induces neuronal apoptosis through integrin β4, ROS, NADPH, and MnSOD.

Collagen modified with epoxidized safrole for improving antibacterial activity

An epoxidized safrole, 5-(oxiran-2-ylmethyl)-benzo[d][1,3]dioxole (OYBD), was synthesized and employed to modify collagen for improving its antibacterial activity. The interaction between collagen and OYBD, and the structure/properties of the modified collagen were investigated in detail. The results indicated that the OYBD-modified collagen showed a higher de-nature temperature (Td, 90.2 °C), improved hydrophobic properties (contact angle from 84.2° to 89.1°) and enhanced tensile strength (6.2-11.0%) without destroying its triple helix structure. From observation of scanning electron microscopy (SEM), a higher density of intertwining morphology and a more stable network structure were observed, which was consistent with improved tensile strength and reduced breaking extension stress. The antibacterial test and LIVE/DEAD Baclight bacterial viability assay illustrated that the modified collagen exhibited excellent antibacterial activity to both Gram-negative and Gram-positive bacteria. Furthermore, the OYBD-modified collagen still exhibited cytocompatibility, supporting human fibroblast proliferation, which holds a great potential for developing antibacterial collagen-based biomaterials.

Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers

Naturally occurring safrole I upon epoxidation gave safrole oxide II, which underwent ring opening polymerization using a Lewis acid initiator/catalyst comprising of triphenylmethylphosphonium bromide/triisobutylaluminum to afford new polyether III in excellent yields. Epoxy monomer II and allyl glycidyl ether IV in various proportions have been randomly copolymerized to obtain copolymer V. A mechanism has been proposed for the polymerization reaction involving chain transfer to the monomers. A strategy has been developed for the deprotection of the methylene acetal of V using Pb(OAc)4 whereby one of the methylene protons is replaced with a labile OAc group to give VI. The pendant allyl groups in VI have been elaborated via a thiol-ene reaction using cysteamine hydrochloride and thioglycolic acid to obtain cationic VII and anionic VIII polymers, both containing a mussel-inspired Dopa-based catechol moiety. During aqueous work up, the protecting group containing OAc was deprotected under mild conditions. Cationic VII and anionic VIII were also obtained via an alternate route using epoxide IX derived from 3,4-bis[tert-butyldimethylsilyloxy]allylbenzene. Monomer IX was homo- as well as copolymerized with IV using Lewis acid initiator/catalyst system to obtain homopolymer X and copolymer X1. Copolymer XI was then elaborated using a thiol-ene reaction followed by F- catalysed silyl deprotection to obtain mussel inspired polymers VII and VIII, which by virtue of having charges of opposite algebraic signs were used to form their coacervate.

Synthesis and characterization of adducts formed in the reactions of safrole 2′,3′-oxide with 2′-deoxyadenosine, adenine, and calf thymus DNA

Safrole (1) is a natural product found in herbs and spices. Upon uptake, it can be metabolized to safrole 2′,3′-oxide [(±)-SFO, 2], which can react with DNA bases to form DNA adducts. The reactions of 2 with 2′-deoxyadenosine (3) and adenine (8) under physiological conditions (pH 7.4, 37 °C) were carried out to characterize its possible adducts with adenine. Four adducts were isolated by reverse-phase liquid chromatography and their structures were characterized by UV/Vis, 1H and 13C NMR spectroscopy and MS. The reaction of 2 with 3 produced two regioisomers, N1γ-SFO-dAdo (4) and N6γ-SFO-dAdo (5), in 4.2-4.5 % yield, and the reaction of 2 with 8 generated N3γ-SFO-Ade (9) and N9γ-SFO-Ade (10) in 1.0-2.4 % yield. Using HPLC-ESI-MS/MS, we traced the amounts of the four adducts formed when calf thymus DNA (10 mg) was treated with 2 (60 μmol) and the levels of 4, 5, and 9 were determined to be 2000, 170, and 660 adducts per 106 nucleotides, respectively. Adduct 10 was not detected under these conditions. These results suggested that stable DNA adducts of 2 were formed in vitro, and further studies on the formation of these DNA adducts in vivo may help to elucidate their role in safrole carcinogenicity. Safrole (1) is naturally present in plants and is banned for use in food additives. The genotoxicity of safrole 2′,3′-oxide 2, which is an in vivo metabolite of 1, has attractedinterest because of its structural similarity to other known epoxide carcinogens. In this work, adenine adducts of 2 have been synthesized and characterized. Copyright

New safrole oxide derivatives: Synthesis and in vitro antiproliferative activities on A549 human lung cancer cells

A number of novel small molecules, safrole oxide derivatives 4a-c, 6a-c, 9a-h, were synthesized by the reaction of safrole oxide with anilines 3 and 5, or its alkyl allyl ether derivative 7 with alkyl bromide 8 in moderate yields. The antiproliferative effects of all the target molecules on A549 cell growth were investigated and it was found that the 14 novel compounds could suppress A549 lung cancer cell growth. Among them, compound 6b was the most effective compound in inhibiting the proliferation of A549 cells.

Method of using calcilytic compounds

The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

A convenient synthesis of 1-aryl-2-propanone precursors of α-methyldopa

A simple two-step approach to 1-(3,4-dimethoxyphenyl)- and 1-[3,4-(methylenedioxy)phenyl]-2-propanone (4a and 4b), useful intermediates for α-methyldopa, is described. It is based on the epoxidation of the widely available methyleugenol (1-allyl-3,4-dimethoxybenzene, 1a) and safrole [1-allyl-3,4-(methylenedioxy)benzene, 1b] with hydrogen peroxide catalyzed by tungsten peroxo complex 2a under two-phase conditions, followed by isomerization of the intermediate epoxides 3a and 3b by lithium iodide.

Quaternary Ammonium Tetrakis(diperoxotungsto)phosphates(3-) as a New Class of Catalysts for Efficient Alkene Epoxidation with Hydrogen Peroxide

The use of quaternary ammonium tetrakis(diperoxotungsto)phosphates(3-) in conjuction with hydrogen peroxide as the primary oxidant in an aqueous/organic biphase system provides an efficient, versatile, and synthetically valuable catalytic method for olefin epoxidation.By this method, a variety of water-insoluble unactivated alkenes, internal or terminal, open-chain or cyclic, isolated or carrying diversified functionalities, were epoxidized in high yields under mild conditions and after relatively short reaction times.

Synthesis of (+/-)-Safrole Oxide

5-Bromo-1,3-benzodioxole (5) on reaction with n-butyllithium in tetrahydrofuran followed by treatment with epichlorhydrin and subsequent quenching by aq.NaOH furnishes a mixture from which 5-oxiranylmethyl-1,3-benzodioxole (2) (safrole oxide) and 5-bromo-4-oxiranylmethyl-1,3-benzodioxole (10) have been isolated and fully characterised.The formation of 2 and 10 clearly indicates that in the reaction of 5 with n-butyllithium, 3,4-methylenedioxyphenyllithium (7) and 2-bromo-5,6-methylenedioxyphenyllithium (12) are generated.