What molecule am I?
The theme of this year’s National Chemistry Week (today through October 25) is “The Hidden Life of Spices”. Accordingly, MOTW brings you myristicin, a natural product found in familiar spices and herbs such as nutmeg (Myristica fragrans), dill (Anethum graveolens), parsley (Petroselinum crispum), and anise (Pimpinella anisum). It occurs in the essential oils of many of these plants.
Myristicin first appeared in the chemical literature in 1890 in an article by Friedrich Wilhelm Semmler at the University of Greifswald (Germany). He isolated the compound from nutmeg oil and mace oil (obtained from arils of nutmeg seeds) and determined its physical properties. In the 1900s, pharmacists O. K. Richter and M. Karmazin confirmed its structure[MB1] .
It was not until 1939 that the synthesis of myristicin was reported. That year, Victor M. Trikojus and D. E. White at the University of Sydney described a three-step synthesis that began with pyrogallol 1-methyl ether1. The authors commented that myristicin is a suitable starting material for synthesizing cotarnine2, an alkaloid that was used to control bleeding from small wounds.
In addition to its presence as a flavoring and aroma constituent of spices, myristicin has been used as an insecticide and acaricide. Adding to its effectiveness against agricultural pests, it has a synergistic effect when combined with other insecticides.
Myristicin’s structure is similar to that of amphetamines; it can cause hallucinogenic effects when administered at doses much higher than are used for cooking. On the positive side, it has shown hepatoprotective effects in laboratory rats, as demonstrated in 2003 by Kimio Sugiyama and collaborators at Shizuoka University and the Kagome Company (Tochigi, both in Japan). They found that of 21 spices fed to rats with liver damage, nutmeg showed the most potent protective activity.
A 2019 study by the National Toxicology Program (Research Triangle Park, NC) on the effects of myristicin on female and male rats and mice showed some minor physiological problems but no substantial adverse effects. No human studies have been performed on myristicin.
1. CAS Reg. No. 934-00-9.
2. CAS Reg. No. 82-54-2.
Myristicin hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Flammable liquid, category 2 | H225—Highly flammable liquid and vapor |  |
| Acute toxicity, oral, category 4 | H302—Harmful if swallowed |  |
| Serious eye damage/eye irritation, category 2A | H319—Causes serious eye irritation | |
| Specific target organ toxicity, single exposure, narcotic effects, category 3 | H336—May cause drowsiness or dizziness | |
| Reproductive toxicity, category 2 | H361—Suspected of damaging fertility or the unborn child |  |
| Short-term (acute) aquatic hazard, category 3 | H402—Harmful to aquatic life | |
| Long-term (chronic) aquatic hazard, category 3 | H412—Harmful to aquatic life with long lasting effects | |
*Safety data sheets vary widely. None shows more than two hazards listed above. Some show no hazards.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. Explanation of pictograms.
Goldene1 is a recently synthesized single-sheet layer of gold atoms, analogous to the carbon allotrope graphene2, the discovery that received the 2010 Nobel Prize in Physics.
The synthesis of goldene was reported in 2024 by Shun Kashiwaya, Lars Hultman, and co-workers at Linköping University (Sweden). The authors began with slabs of gold titanium carbide (Ti3AuC23), a previously prepared substance. They formed goldene sheets up to 100 nm wide by etching Ti3C2 from Ti3AuC2 with Murakami’s reagent4 in the presence of passivating surfactants such as cetyltrimethylammonium bromide5 (CTAB) or cysteine6.
The chemists found that goldene has a strongly contracted in-plane (111) lattice spacing and a gold 4f orbital binding energy increase of ≈0.88 eV compared with bulk gold. Almost immediately after the report by Kashiwaya et al., Bohayra Mortazavi at Leibniz University Hannover (Germany) followed up with a first-principles investigation of goldene. He used theoretical calculations to predict that the gold sheets are thermally stable up to 700 K and that the elastic modulus and tensile strength of the monolayers are >226 and >12 GPa, respectively.
This past June, Giovanni Di Liberto and colleagues at the University of Milano-Bicocca (Milan, Italy) described the use of goldene as a substrate for studying single-atom catalysis. Their work concentrated on transition-metal atoms stabilized on goldene to catalyze hydrogen-evolution and oxygen-evolution reactions. They found that rhodium, ruthenium, and tungsten atoms were promising candidates for hydrogen evolution and that platinum stood out for oxygen evolution.
1. CAS Reg. No. 3084959-31-6.
2. CAS Reg. No. 1034343-98-0.
3. CAS Reg. No. 2095856-60-1.
4. A mixture of potassium ferricyanide and sodium or potassium hydroxide.
5. CAS Reg. No. 57-09-0.
6. CAS Reg. No. 52-90-4.
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Myristicin fast facts
| CAS Reg. No. | 607-91-0 |
| SciFinder name | 1,3-Benzodioxole, 4- methoxy-6-(2- propen-1-yl)- |
| Empirical formula | C11H12O3 |
| Molar mass | 192.21 g/mol |
| Appearance | Colorless to light yellow liquid |
| Boiling point | 276.5 °C |
| Water solubility | Insoluble |
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.
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