Safrol and other allylbenzenes in Australian native plants

[Torsten]

Essential oils of the genus Crowea (Rutaceae).

Leaves of Crowea spp. were collected from Australia. Steam-distilled essential

oils were analysed by GC and GC-MS. C. exalata had 5 chemotypes with principal

components:

(a) safrole (81-88%);

( (E)-methyl isoeugenol (18-25%) and (E)-carpacin (47-51%);

© safrole (27-35%), (E)-methyl isoeugenol (29-46%) and alpha-pinene (12.25%);

(d) safrole (6-29%) and asaricin (57-74%);

(e)1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene (exalatacin; 30-43%) and croweacin

(10-20%).

All chemotypes yielded essential oils in yields of 0.3-1%. The essential

oil of C. saligna contained croweacin (84-94%) as its main component with smaller

amounts of safrole and terpenes. A hybrid, C. exalata X C. saligna, also contained

croweacin (82%) as its main component; its oil was very similar to C. saligna. A

sample of C. angustifolia var. angustifolia produced an essential oil in which the

major components were gamma-asarone (68%), exalatacin (13%) and croweacin (7%).

I am going to build this thread over time with more species. Any input welcome.

[Guest wira]

What's the source of this research? A fresher picture on Crowea has been a long time coming

[Torsten]

TI: Essential oils of the genus Crowea (Rutaceae).

AU: Brophy-JJ; Goldsack-RJ; Punruckvong-A; Forster-PI; Fookes-CJR

SO: Journal-of-Essential-Oil-Research. 1997, 9: 4, 401-409; 24 ref.

I am very intrigued about the exalatacin. Looks like another apiol arrangement.

[Torsten]

Melaleuca squamophloia - Prickly Leafed Tea Tree

"The oil, which is distilled from the leaves, occurs in two chemo types. These major components are elemicin or (E)-isoelemicin."

One form has been tested at a stunning 81% elemicin.

Compared to oil of Elemi, which only has max 20% elemicin, this one might be an interesting commercial crop.

Elemicin is often quoted as the psychoactive constituent of nutmeg and mace oil. While I personally believe both to be psychoactive, little research has been done on this. Obtaining a source of elemicin which is unlikely to contain any myristicin or other related compounds is important for doing meaningful bioassays.

Australia now boasts the premier source plant for mehtyleugenol (Melaleuca bracteata) and elemicin, as well as the only source for exalatacin.

It's a psychedelic wonderland

[mescalito]

Q: Is there a native species of the Sasafrass?

What % safrole etc would be in this genus Torsten?

[Torsten]

There are a few native safrol containing plants, but so far the resarch hasn't been to encouraging in terms of quantity. n fact, the best yields here are probably achieved from the weed Cinnamomum camphora (Camphor Laurel), but only from its rootbark.

As far as natives go, the Atherosperma moschatum seems the most promising, but it is a cool climate plant, so not much research possible for us. There really hasn't been any broad study into the safrol content of different parts of the likely species, and certainly single specimen studies are of limited value. Much to be done.

[planthelper]

as a chippy i can tell you camphor laurel indigestion realy stimulates.

inhaling the fumes, get's you hyperactive.

unfortunately the goodies must be mixed with some nasty stuff, irritating your eyes.

one man's weed is another man's treasure.

even the tasmanian sassafras was once called a weed, because it re-shoots just like camphor laurel.

[mescalito]

Athosperma...cool climate?

That's us :D ,got any pics Torsten? I'll keep my eyes peeled!

[theobromos]

And what is croweacin?

[Torsten]

2-methoxy-3,4-methylenedioxyallylbenzene

you see why I think this might be of interest

[theobromos]

Intriguing.

[nabraxas]

"2-methoxy-3,4-methylenedioxyallylbenzene

you see why I think this might be of interest "--i know you're replying to theo's query, but could you expand on this(because i certainly don't )? is it hush hush or not really relevant to those ov us outside chem labs?

[Torsten]

well, the 3,4 methylenedioxy bridge is the same that is in safrol and is the bit that makes the common effect of MDA and MDMA as magical as it is.

The 2 position which in this case is occupied by a methoxy group is in most cases not significant. It may or may not add a different aspect to the experience of either the oil (via biogenic amination)or the semisynthetic aminated derivatives.

The number two substitutions are of significance in one of the PEA series though, so who knows what might happen here.

It would be nice to make the oil available to the general public in the hope that some of it may find its way into capable hands.

[nabraxas]

thanks t. that's a bit clearer; i'm sorry to bother you more, but what would "capable hands" be expected to do w/the oil?---i'm guessing that by "capable" you mean 'w/access to a fully equiped chem lab'.

more importantly, is there anything 'incapable hands' could safely do w/the oil?

[Torsten]

Originally posted by nabraxas:

what would "capable hands" be expected to do w/the oil?---i'm guessing that by "capable" you mean 'w/access to a fully equiped chem lab'.

something like that, yes. I don't think equipment is really the big issues, but rather other ingredients.

is there anything 'incapable hands' could safely do w/the oil?

I used to experiment with sassafras and nutmeg oil both by ingestion and by rubbing into muscles, to get appropriate effects. There is plenty of stuff I have written about that on these forums. I figure, the first thing I would do once I get the oil is to massage it into my leg muscles and then go for a run.

[nabraxas]

indeed, you have posted on using sassafras and nutmeg oil before; i'm just too dim to make the connection. thanks.

would you post the results ov your imaginery jog when/if it happens?

[Torsten]

there is nothing illegal about the jog, so it doesn't have to be imaginary. That's the interesting thing about the experiments with oils.

[planthelper]

talking native oils...

whats the story with zieria spp. containing high levels of myristicin?

apart for mozzie control, por favor.

[Torsten]

yes, Zieras can be very interesting. Lots of different species and chemical races though.

[Torsten]

Got some Cinnamomum laubattii plants the other day and the leaves when crushed emit a strong safrole odour, followed by bubble gum odour. The latter is probably methyl-eugenol as it smells very similar to Melaleuca bracteata (which is rich in methyl eugenol).

Pity this native species is rather rare.

[Tree]

 

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posted 21. September 2003 01:34

 

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Got some Cinnamomum laubattii plants the other day and the leaves when crushed emit a strong safrole odour, followed by bubble gum odour. The latter is probably methyl-eugenol as it smells very similar to Melaleuca bracteata (which is rich in methyl eugenol).

 

Pity this native species is rather rare.

 

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We have a small tree in the backyard that has an almost overpowering smell of "bubblegum"when it flowers. It is flowering now -refer to photos below. We don't know the plants ID, any ideas? Could be useful

Thanks

[Andrew]

Dont know about the pictures but it

sounds like maybe its a magnolia.

[mescalito]

That was my guess??

[planthelper]

yes, looks like a port wine magnolia, michelia fuscata.

[Tree]

Spot on planthelper, it is a michelia fuscata and belongs to the Magnolia family - So you all got it right .

The plant comes from China and as a result does not belong in this forum . Sorry to hijack the thread but the smell is sooo "bubblegum" and I couldn't resist. Anyhow I have an ID.

Thanks again. Take care.