Isosafrole from red cedar?

[goldmember]

https://www.thevespiary.org/rhodium/Rhodium/chemistry/safrolefaq.html

I was reading this and noticed that juniper virginiana leaf oil contains isosafrole... I don't know if the sawdust would contain much of the essential oil, but SWIM grew up on a farm and used to get the sawdust (AKA "shinglehair" because it's the sawdust leftover from making shingles) by the truckload for horse bedding, it was fairly strongly scented, so I suspect it would contain at least some essential oil.

Safrole is bad karma now, and steam distillation is easy, and it would be hard to beat $25 for a truckload of isosafrole-containing sawdust.

I think it's definitly worth looking into.

[Hedonist_Rex]

The oil from the foliage is said to contain ~11% safrole and ~6% isosafrole, but I've been told the wood oil does not.  I'd love to be wrong... cedarwood oil is cheap, like $50/kg (and unwatched). 

While we're on the topic, SWIM is interested in distilling oil from the foliage (it's everywhere).  The safrole faq says This gave us a list of approximately 140 distinct molecules which came off the column, I left most of them off.

Does anybody have the full list of constituents and their percentages?

[sYnThOmAtIc]

JUNIPER leaves - juniper virginiana
Table below: representative volatile leaf oil composition for junipers (J. virginia var virginiana (USA), eluted from a DB-5 gas chromatography column. Data expressed in % of total oil, the oil derived from steam distillation of the FOLIAGE. (so no digging-up of the roots is required).

This gave us a list of approximately 140 distinct molecules which came off the column, I left most of them off.

The significant numbers are marked in red

RT(s) Compound %  B.P. (deg C) from Merck, 12th edn.
319 alpha-pinene 1.4 bp20:52.5 bp760:155-156
379  sabinene 6.7 No Listing
408  myrcene 0.9  beta from: bp10:44
481  limonene  18.9 bp763:175-176
608  terpinolene 0.5  No Listing
632  linalool  4.4 (dl) 194-197
734  camphor  3.7 mp:179 bp204
789  borneol  0.8  mp:(d)208 (l):204 bp:(d) 212:(l) 210
820  4-terpineol 1.5  bp:206-219 (d, l, and dl)
1101 safrole  10.9  mp:~11 bp:232-234
1229 cis-isosafrole 6.7  mp:~8.2 bp760:253 bp100:179.5
1403 methyleugenol  2.9 No Listing
1700 delta-cadinene 0.8 bp9:124

RT = retention time on the DB-5 column.

I gather this tree is known as the Red Cedar, though I think there are probably several trees which come under this moniker so there is room for confusion. It is also supposed to be the source of Red Cedarwood Oil, though the safrole content of this is unknown. Cedarwood oil is used for immersion
lenses in high-magnification microscope work.

Note: the incompetants at AUROMA Australia will supply you with the leaf oil of the communis species when you ask for the virginiana type. Ellisons of Nowra sell the seeds to this plant, which have reliably germinated.

 


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[sYnThOmAtIc]

atlantone, caryophyllene, cedrol, cadinene everything else is inthe 3%-.1% range

[Hedonist_Rex]

Does anybody have the full list?  127 constituents, making up 40% of the oil were "left off".  (why?)

Can it be assumed the others are low boiling point fractions no where near safrole or iso?

Is it worth saving anything else as precursors for other possibly interesting synths?