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Pheromones鈥攈ormonal substances that animals and some other organisms emit to attract or warn other members of their species鈥攁re well known today. But it has been only 鈮�60 years since they were first discovered and characterized. Bombykol, a sex pheromone released by female silkworm moths such as Bombyx mori and B. mandarina, was the first one to be studied thoroughly.
The pioneering work on bombykol was done by Adolf Butenandt and his co-workers at the Max Planck Institute of Biochemistry (Munich). He named the molecule after the silkworm genus, determined its structure, , and demonstrated that its effects duplicated those of the natural product. Twenty years before his work on bombykol, he was awarded the 1939 Nobel Prize in Chemistry for his research on other sex hormones.1
From Butenandt鈥檚 time until now, much research has been done on the biochemistry of bombykol:
- In 1987, Tetsu Ando and colleagues at the Tokyo University of Agriculture and Technology .
- In 1995, Shogo Matsumoto and co-workers at the Institute of Physical and Chemical Research (RIKEN) (Saitama, Japan) reported a biosynthesis of the compound .
- In 1999, Jon Clardy and coauthors at Cornell University (Ithaca, NY) and the National Institute of Sericultural and Entomological Sciences (Tsukuba Science City, Japan) protein in the male B. mori that binds bombykol emitted by the female.
Finally, in 2020, Jean-Fran莽ois Dufr锚che and collaborators at the University of Montpellier Marcoule (Bagnols-sur-C猫ze, France) and CNRS鈥揢niversity of Tours (France) proposed a theory for how pheromone molecules are transported in an atmosphere that contains aerosols鈥攅ven though many pheromones are hydrophobic. as a model compound in their study.
1. Butenandt was affiliated with the Nazi party, which in the years after World War II.
Bombykol hazard information
Hazard class* | GHS code and hazard statement |
---|---|
Not a hazardous substance or mixture | 听 |
*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.
MOTW update
(鈥�)-厂迟谤测肠丑苍颈苍别1 was the Molecule of the Week for December 2, 2013. It is a virulent poison produced in the seeds of plants of the Strychnos genus. Its non-natural enantiomer, (+)-strychnine2, was first synthesized in 1995.
In the 1940s, Robert Robinson (Oxford University) and Robert B. Woodward (Harvard University), both eventual Nobel laureates in chemistry, published structures of the natural strychnine molecule. Since then, there has been controversy as to which chemist should be credited for first describing the true structure.
In a recent survey of chemists conducted by Jeffrey I. Seeman* at the University of Richmond (VA) and Mark C. House at Santa Fe College (Gainesville, FL), the respondents did not reach a consensus as to which Nobelist deserves the credit. The authors concluded that
1. CAS Reg. No. 57-24-9.
2. CAS Reg. No. 163956-38-5.
Molecules from the Journals
MOTW briefly describes noteworthy molecules that appeared in recent ACS journal articles. See this week's edition.
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Bombykol听fast facts
CAS Reg. No. | 765-17-3 |
nomenclature | 10,12-Hexadecadien-1-ol, (10E,12Z)- |
Empirical formula | C16H30O |
Molar mass | 238.41 g/mol |
Appearance | Colorless to light yellow liquid |
Boiling point | 130鈥�133 掳C (0.005 Torr) |
Water solubility | 鈮�0.2 mg/L (est.) |
Molecules from the journals
Ritonavir1 is an older antiretroviral drug developed at Abbott Laboratories (North Chicago, IL) in 1990 and approved by the US Food and Drug Administration in 1996. Nirmatrelvir2 is much newer; it was developed in 2021by Pfizer (New York City) from a previous drug candidate. Later that year, FDA granted Pfizer an emergency use authorization for a combination of the two drugs for treating COVID-19 under the trade name Paxlovid. Read how Pfizer scientists developed Paxlovid .
This past May, Deyin Wang, Yuhua Wang, and co-workers at Lanzhou University (China). reported a of the complex salt Cs3MnBr53, a blue-light鈥揺xcitable, narrow-band, green-emitting phosphor. The phosphor had been made previously, but the authors believe that their convenient synthesis will make it a prime candidate for backlighting in white-light鈥揺mitting diode displays.
1. CAS Reg. No. 155213-67-5.
2. CAS Reg. No. 2628280-40-8.
3. CAS Reg. No. 2768353-64-4.

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