Christmas Chemistry: Synthesis of an Essential Oil from Myrrh

[NNadir]

It's probably not entirely Kosher for an atheist to comment on Christian Scriptures, but as a cultural affectation, based on my Christian upbringing and my long participation in American consumer culture, I will anyway.

If there are responses to this post, they are likely to contain clips from Monty Python's Life of Brian.

From the "Molecule of the Week" from the ACS, Furanoeudesma-1,3-diene, the active component from the resinous oil Myrrh which was reported as a Christmas gift from the "Three Wise Men."

Furanoeudesma-1,3-diene

(The world could use three wise men now, but we only have one, Joe Biden.)

From the text, the link, not the Bible:

Myrrh is a resin that occurs in some species of trees in the genus Commiphora that grow in Asia, Africa, and South America. Myrrh is especially prevalent in C. myrrha, which grows in the Arabian Peninsula (Oman and Yemen) and northeastern Africa (Djibouti, Ethiopia, Somalia, and northeast Kenya).

Myrrh resin and the oil derived from it have been used for millennia as a fragrance and medicine. Along with frankincense1, it is familiar as a gift offered to the Christ child by the Magi in the Christian gospel.

In 1983, Carl Heinz Brieskorn* and Pia Noble at the University of Würzburg (Germany) identified furanoeudesma-1,3-diene and two other aroma compounds in the essential oil of myrrh. Thirteen years later, Jose R. Pedro and co-workers at the University of Valencia (Burjassot, Spain) described the stereoselective synthesis of furanoeudesma-1,3-diene from the drug santonin2. The synthetic product was identical to furanoeudesma-1,3-diene obtained from C. myrrha...

I've called up the 1983 paper to enjoy how far we've come since then with structure elucidation. (It was fine work for its time.)

The synthesis from a starting material chemically derived from the antiparasitic drug Santonin was described here:

Stereoselective Synthesis of 8,12-Furanoeudesmanes from Santonin. Absolute Stereochemistry of Natural Furanoeudesma-1,3-diene and Tubipofurane Gonzalo Blay, Luz Cardona, Begoña García, José R. Pedro, and Juan J. Sánchez The Journal of Organic Chemistry 1996 61 (11), 3815-3819.

The synthetic scheme:



The compound is reportedly a pain killer and has been been demonstrated to bind to opioid receptors. Whether it is, as many such binding compounds are, is not for me to say.

The Christmas season is addictive however. I celebrate it every year in the traditional consumer oriented way.

I wish you a Merry Christmas or holiday of your cultural choice and a happy, healthy and prosperous New Year in which we can celebrate the reelection of Joe Biden.

[erronis]

1. Thanks for the holidaze wishes and this bit of chemical wizdom.

Always enjoy reading your posts - some I understand a bit of!

[yowzayowzayowza]

2. Right back atcha. Thank you, Sir. n/t