# Chemical components of eucalyptus EO



## galaxyMLP (May 29, 2015)

So, I said I would do it and I did! I took 2 types of eucalyptus oil, GC/MS'ed them at work (on my last night on the night shift) and compared the resulting compounds. 

A brief overview of a GC MS.

 A GC is a gas chromatograph. It takes a volatile compound, turns it to vapor, sends it into a column to be separated into its components, and passes onto a detector. Components are separated mostly by boiling point of the various compounds because the temperature ramps up as the time goes on (for my application).   The column is very thin and made of silica [essentially glass]) that is about 90 feet long (it is wrapped into a coil). The internal diameter is less than 1 millimeter.
The system is hooked up to a detector that detects different compounds as little peaks. The combination of all peaks in one sample is called a chromatogram.

The MS (mass spectrometer) allows one to identify these peaks because it is an additional detector that breaks apart the molecules into smaller parts and creates a "fingerprint" for each peak. Each of these finger prints is compared to an existing library to find matching compounds.

I used now foods eucalyptus EO and a cheap eucalyptus EO made by a company called sanvall that I thought might have been adulterd (even though it smelled great it was just very cheap, $1.97 for a 1 oz bottle) 

I can post the chromatograms for those that are interested in later comments but for now I will just list the identifiable (no less than 0.01%) components in each. 

NOW foods:
In order of elution in the chromatogram:
- alpha phellandrene
- R-alpha- pinene
- sulcatone
- camphene 
- beta pinene
- alpha phellandrene
- terpinolene
- *D- limonene/ Eucalyptol  major component
- Y-terpene


Sanvall
-alpha thujene
- alpha pinene
- camphene
- beta myrcene
- beta pinene
- cymene (p-cymene)
- *Eucalyptol/d limonene (Major component)
- y terpene
- linalool

*Eucalyptol/D-limonene came out as one peak although I was able to see them separated enough to identify both of them. 

I actually like the way the sanvall smells better. It has more citrus and minty top notes (this is due to the greater amount of pinene/thujene) 

I was surprised as how different the 2 eos were even though they were the "same". I could've run on a longer column to resolve (separate) the d limonene and Eucalyptol but I didn't feel like it!


ETA:
Ok, later today I'm going to post about each of those compounds and what they are/where they are most commonly found. 

I will also be posting what chemicals are in highest proportional order (I realize that is the way that would make most sense now!)


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## Dr.J (Aug 12, 2015)

Interesting, thanks for posting.

I recall finding a paper on GC-MS examination of Eucalyptus Globulus that might be of interest – available here

I’ve been wanting to do some similar work testing ground lavender buds versus lavender EO by headspace GC-MS to see “what’s missing” in the EO. Unfortunately I don’t know enough about the technique to run it myself, and I’m also worried about the implications of getting caught by my employer.

If you have other data, please share as I will certainly appreciate it. Maybe others too?


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## galaxyMLP (Aug 12, 2015)

We are actually supposed to get a brand new headspace in the next year or so at my current position/job. I have lots of ideas of EOs to run (not that it will probably happen). 

I haven't had a chance to run anymore on the GC MS. I'm in a different area of my site now (got offered a job that wasn't on nights) so I don't have the time/capability to run anymore.


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## Saponista (Aug 13, 2015)

I used to use one for analysing lipid content of algae. I hated changing the column so I can see why you didn't want to put a longer one on to resolve the other peaks. It's really interesting to see the differences. I guess it's due to the fact that even though the eucalyptus plants look the same there are big genetic differences between crops in different areas. In our algal strains that were so closeley related that you would never tell them apart microscopically and were pretty much identical genetically, the lipid profiles were quite significantly different, and could be altered even in the same strain by simply changing nutrient levels and growth conditions.


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## Spice (Aug 14, 2015)

So what is the purpose? I dont understand.:eh:


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## galaxyMLP (Aug 14, 2015)

Saponista, actually I was really just being lazy becasue we have 2 GC-MS with 2 columns each (4 diff total). It was just going to take an hour more per essential oil. That's very interesting about the algae. I guess it makes sense that nutrient content can effect lipid profile. I would think nutrients high in nitrogen would produce different lipids than a nutrient uptake low in nitrogen but high in something else.

 Spice, this is sort of "just for fun" and interesting to see. Both are 100% eucalyptus essential oil yet the chemical nature of them differs pretty significantly which is why they smell different. I just wanted to see if I could identify the compounds/notice any differences and I did!


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## DeeAnna (Aug 14, 2015)

Spice -- a gas chromatograph (GC) is a special kind of machine only found in a chemistry lab. A GC takes a lot of care and fussing to keep running properly, but it is a pretty cool machine because it can tell you what specific chemicals are included in a particular essential oil (or other chemical blend). In this case, Galaxy tested two different kinds of eucalyptus EOs to see what blend of chemicals make up each EO. 

Sometimes, if you know what to look for, you can tell if an EO has been contaminated or adulterated with chemicals that are not naturally found in a EO that comes from plant material only. You wrote in another thread about sandalwood, and I know sandalwood is often adulterated with synthetic chemicals. A GC can be used to figure that out.

Sometimes, if you know what to look for, you can tell what EO came from what part of the world or even what variety of eucalyptus tree was used to make a particular EO. 

And sometimes, again if you know what to look for, you can tell from the GC results why you like the smell of one EO more than the smell of another. In this example, Galaxy likes the smell of the "Sanvall" EO because it smells more pine-y and citrus-y. These smells come from chemicals called pinenes.


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## galaxyMLP (Aug 14, 2015)

^^^^ This, exactly what Dee said. 

Thank you soooo much Dee!  You are a lifesaver. Sometimes I don't know how in depth to get but somehow you always seem to go in depth just enough to explain things! Love it! 

I often forget how to explain things/what someone may be trying to get out of an explanation/ question, and it is especially difficult in a forum setting. Again, thanks!


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## TeresaT (Aug 14, 2015)

^^^^^I'm glad DeeAnna answered Spice before a I had the chance.  My answer?


  "They're lab geeks.  We're not supposed to." 

(I <3 you two.  I learn, and get confused by, more stuff than I ever did in high school.)


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## DeeAnna (Aug 14, 2015)

It comes from a couple of decades of training people to run chemical plants and then teaching math and science to reluctant freshman and sophomore college students. I can fairly well follow what you (Galaxy) and Saponista are talking about, but I can also appreciate the viewpoint of someone who has never even seen a GC. It's a fun challenge to bridge between both worlds. I suppose it's similar to what a language translator does, although I can't speak a second language to know that for sure. 

It's been quite awhile since I messed around with a GC so I remember the general concepts, but not any specifics. That means you two -- Galaxy and Saponista -- are going to have to explain the details if anyone asks!


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## Saponista (Aug 15, 2015)

I am so not the person to ask. I'm really not a chemist but had to use the gc-ms as there was no one else to do the work. My knowledge is very limited! I was terrified while using it that I would do something wrong and mess the whole thing up. I'm much more at home doing molecular biology with pcrs and trawling through sequence data 

I would be really interested to compare rose geranium EO's though. I'm sure they adulterate the cheaper ones. I had an expensive bottle which smelled really floral and light and was a really pleasant smell. My soap didn't seize and after cure I was really happy with the soap. However the cheaper stuff seizes and smells what I can only describe as slightly pungent. It would have been really interesting to see the difference in profile and whether it had been diluted with something unpleasant.


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## galaxyMLP (Aug 15, 2015)

*Geeking out ahead, sorry in advance!*

Wow, that would be interesting!! If someone sends me samples maybe I could try that... Hmm. I still have a good relationship with the people in that lab so they might let me run something. EOs are pretty gentle on these instruments.

I really do love my chromatographic instruments. Whenever we get a new one (liquid or gas) its so exciting! Ok, scratch that, I love new chemical instruments in general. 

Saponista, I had a class once where we did pcr and I had to look at sequences ect. But its honestly pretty foreign to me! We had to identify certain sequences for certain traits in a plant tissue sample.

 I made a boo-boo during the DNA extraction and the conical tube I was using EXPLODED in my face. Needless to say, DNA extraction isnt my thing. I ended up going to the infirmary and they had to write a report. I also learned to use the eye wash and at the same time my professor decided I needed the shower too. At least now I'm not afraid of using the eye wash anymore. Good times...


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## Saponista (Aug 15, 2015)

Was it a phenol chloroform extraction? If so I can see why having your face splattered in phenol may not have been the wisest of moves! I don't have any of the nice rose geranium left but if I get some more I will try and send it to you as I am genuinely really interested in the analysis.

I am also no novice to the eye wash. I dropped a glass bottle of acetone and it splashed into my eye and I got sent to the eye hospital. I didn't have goggles as I wasn't even planning on opening it! I also spattered random bacterial samples into my eye on another occasion. I still hate getting my eyes washed out though, it's not a pleasant experience!


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## galaxyMLP (Aug 15, 2015)

No its not fun! And I don't think phenol was in there but we did have some mercaptoethanol in there so I stunk all day. It exploded from pressure building after grinding the plants in liquid nitrogen. It was so violent that the tube basically shattered and the contents were flung onto the roof. 

Acetone and bacteria... Yum. Lol. Glad it sounds like you were ok after that though.


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## Saponista (Aug 15, 2015)

We used to prank each other by filling the eppendorfs with liquid nitrogen and dropping them in people's pockets. It goes off with an almighty bang lol! I probably shouldn't admit to that!


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## Spice (Aug 16, 2015)

Saponista said:


> We used to prank each other by filling the eppendorfs with liquid nitrogen and dropping them in people's pockets. It goes off with an almighty bang lol! I probably shouldn't admit to that!


that's funny.


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## Spice (Aug 17, 2015)

DeeAnna said:


> Spice -- a gas chromatograph (GC) is a special kind of machine only found in a chemistry lab. A GC takes a lot of care and fussing to keep running properly, but it is a pretty cool machine because it can tell you what specific chemicals are included in a particular essential oil (or other chemical blend). In this case, Galaxy tested two different kinds of eucalyptus EOs to see what blend of chemicals make up each EO.
> 
> Sometimes, if you know what to look for, you can tell if an EO has been contaminated or adulterated with chemicals that are not naturally found in a EO that comes from plant material only. You wrote in another thread about sandalwood, and I know sandalwood is often adulterated with synthetic chemicals. A GC can be used to figure that out.
> 
> ...





galaxyMLP said:


> ^^^^ This, exactly what Dee said.
> 
> Thank you soooo much Dee!  You are a lifesaver. Sometimes I don't know how in depth to get but somehow you always seem to go in depth just enough to explain things! Love it!
> 
> I often forget how to explain things/what someone may be trying to get out of an explanation/ question, and it is especially difficult in a forum setting. Again, thanks!



You guys rock! That is amazing how all that chemical stuff works. Thank you so much for the insight, I was wondering why so much work and all that in depth research. It now brings the eos into a brighter light for me. How very interesting.:clap:


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## Spice (Aug 17, 2015)

Saponista said:


> I used to use one for analysing lipid content of algae. I hated changing the column so I can see why you didn't want to put a longer one on to resolve the other peaks. It's really interesting to see the differences. I guess it's due to the fact that even though the eucalyptus plants look the same there are big genetic differences between crops in different areas. In our algal strains that were so closeley related that you would never tell them apart microscopically and were pretty much identical genetically, the lipid profiles were quite significantly different, and could be altered even in the same strain by simply changing nutrient levels and growth conditions.


I cant believe that now that I know what is happening I can understand in my mind the concept of a plant and its inviro. I dont want to sound like I am trying to be a geek, but I have always looked at origin when I order eos. I also noticed that some eo cost more from different countries too. :razz:


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## Dr.J (Aug 19, 2015)

Another comparison I've always wanted to do by GC-MS is the overpriced, hyped brands (like Dotera and Young Living) vs. the more affordable good stuff from folks like NDA, etc.

I wish y'all would get to work.


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## galaxyMLP (Sep 1, 2015)

Because some people showed interest and because I'm interested in it as well. I did this same experiment with 2 types of lavender EO. I did this with lavender EO from Now foods and Radha Lavender EO (found on amazon).

Now foods (NF) Lavender EO is supposedly French lavender EO whereas Radha is bulgarian lavender EO. The Radha (R) brand is much much cheaper so I wanted to know if it was adulterated with something. NF is a more herbaceous lavender while R is more floral.

Findings:
Neither lavender is adulterated. They both have a very similar profile except for a few differences.

Both contained: Eucalyptol, linalool, linalyl acetate, Caryophyllene, octanone, borneol, and lavendulol

NF has camphene but R does not. Camphene is the main component of camphor oil. This leads me to believe that if you want that more "herbaceous" lavender sent, you can add a bit of camphor oil.

R has many more terpines (lime-y scents) in it. It had alpha terpene, y-terpene, myrcene, omicene. But, NF only had one or two terpines along with D-limonene (main component of lemon EO) in a small amount.

This is all very interesting because it can give you a good idea of what will blend well with lavender.

For example, if you like a more floral lavender, it may be wise to add a bit of lime EO since lavender that is more floral naturally contains more lime-y scents (those are the terpines). 

Now, if you want a more herbaceous lavender, you can add camphor oil to it or even a bit lemon EO since D-limonene is the main component of lemon EO.

Both of them contain eucalyptol which leads me to believe that lavender eucalyptus would be a wonderful scent combo.


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## Saponista (Sep 1, 2015)

This is so interesting. Thank you Galaxy!!!! Please do more if u get chance.


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## galaxyMLP (Sep 1, 2015)

I actually don't have that many EOs... I'm going to have to get some more just for these tests. Are there any suggestions on what to compare next? I have 2 types of tea tree oil but they really do smell the same to my nose. What would any of you all like to see here? 

If someone has spanish lavender EO I could do a comparison with that as well. I would test the FO's but since they have much higher boiling points, I'd be afraid to gunk up the instruments. So for now its just EO's. 

Had a thought: What about 10x orange, 5x orange and sweet orange? I only have sweet orange. Anyone close to me got some 10x or 5x to spare?


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## kchaystack (Sep 1, 2015)

That is too bad about FO's.  It would be interesting to see a comparison between sandalwood EO and FO to try and find out how to best dupe it.

I don't use much EO.  Peppermint, tea tree, and lemongrass.  

Maybe a compare between lemongrass and other citrus?  Just brainstorming.


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## not_ally (Sep 1, 2015)

Galaxy, I recently visited Jo Lasky of Fragrance Labs, one of the things she showed us (in the context of aroma chemicals) was this great book which listed commonly used e.o.'s in fragrance making and broke them down into their chemical constituents (not sure if I am describing this right) which is helpful for blending A/C's as well as EO's.  I don't have the name of it, I did write it down but my notebook is in boxes of stuff that is all spread around b/c I am moving.  

It was a rare book and expensive, but she said that it was worth it, you might want to email her (or PM JBlaney, she was there as well) to see if it was something that you might like.

ETA:  I just realized, this might not be that helpful if you are comparing different types/sources of the same EO, though, sorry.


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## not_ally (Sep 1, 2015)

Saponista said:


> We used to prank each other by filling the eppendorfs with liquid nitrogen and dropping them in people's pockets. It goes off with an almighty bang lol! I probably shouldn't admit to that!



Man, you science geeks know how to have fun!  Said fondly   My dad is a molecular biologist, and he can crack himself up (and us too, just by how hard he is laughing) at this stuff as well.


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## galaxyMLP (Sep 1, 2015)

Thanks NA, I'll have to look into that! Sounds like an interesting book!

Oh, and K, I wish I could do FOs but I really shouldn't. I'd love to try a lavender FO vs the real deal or as you said, sandalwood (although getting the real deal would be next to impossible!) I like the lemongrass idea. I have live lemongrass. I'll try extracting some oil from it in alcohol and run it against some lime eo. Or if someone has lemongrass eo they want to donate to science, that works too!


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## TeaLeavesandTweed (Sep 3, 2015)

I'd also be curious to see what rose FOs compare to real rose otto or absolute, but I imagine I would have to foot the bill for that one. So, yeah, not that curious.


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## galaxyMLP (Sep 3, 2015)

Haha, I would absolutely love to know that too! I think 5% rose absolute is not too bad. I might actually try that one.... maybe one day. 

I thought of that one a while ago. I have a nice rose FO but it certainly doesnt smell like a true rose.


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## TeaLeavesandTweed (Sep 3, 2015)

galaxyMLP said:


> Haha, I would absolutely love to know that too! I think 5% rose absolute is not too bad. I might actually try that one.... maybe one day.
> 
> I thought of that one a while ago. I have a nice rose FO but it certainly doesnt smell like a true rose.



I found a 10% rose otto mixed in argan oil on Etsy from an EO seller that a like a lot. I've thought of buying it as a hair serum. She also does 10% jasmine (grandiflorum) in argan, so I can't make up my mind.

I love the scent of roses, but I had a bad reaction to a fragrance in a handmade soap in the past and don't really feel like patch testing any FO I buy for a month with the possibility of randomly erupting in hives again. I have one FO-based product that I love enough to risk it and it turned out alright. It might be worth it again if I had a really nature-similar FO to try...


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## DeeAnna (Sep 5, 2015)

I have a 10% to 20% dilution of rose EO in jojoba. At that dilution, it's really pungent, and I wouldn't dream of using it on my body. I use this diluted EO at 0.5% or less in lotion and the scent is more rose-like and pleasant at a very low %. That stands to reason -- the % of rose aroma that you get from a real rose is minuscule too!

Does this rose EO really smell like roses? In a word, no. EOs do not contain the water-soluble portions of a scent, and those tend to be the floral, sweet components of the overall scent. Most EOs are not as floral as the plant from which the EO comes -- the scent of lavender EO is a prime example that most people would have experienced.


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## rparrny (Sep 5, 2015)

I thought some might find this interesting and useful.  Years ago I was fortunate enough to spend some time with Jim Duke at his home and "green pharmacy" and during that trip he told me about the database he created on herbs and although it's not classified or anything, it's not advertised to the general public but anyone with the web address can access it.  I find it very useful.  Here's the link: http://www.ars-grin.gov/cgi-bin/duke
And here's a search on eucalyptus:  You can click on hyperlinks to learn all kinds of stuff like actions ect...
For those of you wanting to learn more about herbs but not knowing where to start, I highly recommend "The Green Farmacy", Jim's most famous book...but honestly they are all great.  He is basically the reason herbs are now being taken seriously by "modern medicine"...a wonderful man with a great sense of humor...
Years ago, I wanted to start a very malnourished patient on some alfalfa extract but the pharmacy wouldn't approve it because "we don't know what it's composed of"  I replied "I do" and sent them the list like the one below...they still denied it but when asked why they were very embarrassed to admit they didn't have a reason...

*Dr. Duke's
     Phytochemical and Ethnobotanical Databases*







*Chemicals in:   Eucalyptus citriodora HOOK.  (Myrtaceae) -- Citron-Scented Gum, Lemon Eucalyptus, Lemon-Scented Gum, Spotted Gum*

*Chemicals*


*1,8-CINEOLE* _*Leaf*_ _50 - 3,580 ppm_ DUKE1992A 
*7-O-METHYLAROMADENDRIN* _*Plant*_:   DUKE1992A 
*ALPHA-PINENE* _*Leaf*_ _5 - 380 ppm_ DUKE1992A 
*AROMADENDRENE* _*Leaf*_:   DUKE1992A 
*AROMADENDRIN* _*Plant*_:   DUKE1992A 
*BETA-PINENE* _*Leaf*_ _20 - 300 ppm_ DUKE1992A 
*BETULINIC-ACID* _*Leaf*_:   JAD _*Plant*_:   DUKE1992A _*Root*_ _166.7 ppm_;   JAD 
*CAMPHENE* _*Leaf*_ _1 - 20 ppm_ DUKE1992A 
*CARVONE* _*Leaf*_:   DUKE1992A 
*CARYOPHYLLENE* _*Leaf*_ _15 - 780 ppm_ DUKE1992A 
*CITRAL* _*Leaf*_:   DUKE1992A 
*CITRONELLAL* _*Leaf*_ _50 - 18,020 ppm_ DUKE1992A 
*CITRONELLOL* _*Leaf*_ _230 - 4,000 ppm_ DUKE1992A 
*CITRONELLYL-ACETATE* _*Leaf*_ _20 - 130 ppm_ DUKE1992A 
*EUDESMOL* _*Leaf*_:   DUKE1992A 
*EUGENOL* _*Leaf*_:   DUKE1992A 
*GERANIOL* _*Leaf*_ _250 - 1,000 ppm_ DUKE1992A 
*GUAIACOL* _*Leaf*_:   DUKE1992A 
*GUAIOL* _*Leaf*_:   DUKE1992A 
*HYDROXYCITRONELLAL* _*Leaf*_:   DUKE1992A 
*ISOPULEGOL* _*Leaf*_ _35 - 5,960 ppm_ DUKE1992A 
*LIMONENE* _*Leaf*_ _20 - 1,420 ppm_ DUKE1992A 
*LINALOL* _*Leaf*_ _15 - 180 ppm_ DUKE1992A 
*MYRCENE* _*Leaf*_ _1 - 120 ppm_ DUKE1992A 
*NEO-ISOPULEGOL* _*Leaf*_ _20 - 680 ppm_ DUKE1992A 
*P-CYMENE* _*Leaf*_ _10 - 180 ppm_ DUKE1992A 
*TERPINENE* _*Leaf*_ _1 - 180 ppm_ DUKE1992A 
*TERPINOLENE* _*Leaf*_ _5 - 160 ppm_ DUKE1992A 
*URSOLIC-ACID* _*Plant*_:   DUKE1992A   Ubiquitous chemicals not included in analysis
ppm = parts per million
    tr = trace
	

	
	
		
		

		
		
	


	



 Sat Sep  5 10:31:18 EDT 2015 
      Please send questions and comments to:

*James A. Duke* 
Green Farmacy Garden 
8210 Murphy Road 
Fulton, MD 20759 

or  *Mary Jo Bogenschutz*     (E-Mail:      [email protected])            Dr. Duke does not recommend self diagnosis or self medication.      Please see the disclaimer     for more information.


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## galaxyMLP (Sep 6, 2015)

Interesting. I don't have permission to view it though. Ah well, its ok. Thanks for the additional information!

And Dee, considering 2000 lbs of roses make 1 oz of EO, I was guessing that very, very little rose EO goes a long way. It's also interesting that rose hydrosol and other plant hydrosol also contain so many components of a flowers fragrance but that we don't have access to them since they are water soluble and don't enter the oil. I think that's a case when FOs really are great.


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## DeeAnna (Sep 6, 2015)

"...I was guessing that very, very little rose EO goes a long way..."

That guess is spot-on in my experience!  I have heard that CO2 extracts are often more true to the real scent than a solvent or distilled EO. I have no experience with this, so just passing on what I've read from reasonably reputable sources.

On a related note -- I did a hydrosol and an oil infusion of sweet grass (Hierochloe odorata) this summer. I've made infusions before, but this was my first try at making a hydrosol, and I know I have a lot to learn about that art, but I didn't do too bad for a first timer. I learned the odor of the sweetgrass is split between the fat soluble molecules (more of the hay-grass odors) and the water soluble ones (more of the sweet, spicy odors). 

Nothing of the sweetgrass scent seem to come through when the infusion or hydrosol is used in soap. I didn't expect any success, actually, but I needed to try it once to confirm. I'll stick with using a sweetgrass FO to get an appropriate scent in the soap. Now that I know what the hydrosol smells like, I realize the FO, which is sweet, green, and slightly spicy, smells much more like the hydrosol than the overall scent. The hay-grass undertone of the real sweetgrass is absent in the FO. That's not all bad -- I can live with that.

ETA: Try this for the Duke database: http://www.ars-grin.gov/duke/


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## Dr.J (Dec 5, 2015)

For my fellow nerds who find this topic interesting:

I recently acquired a textbook that greatly details the chemical composition of many EOs, with lots of other great info that I'd like to recommend to you:

"Essential Oil Safety", 2nd edition, by Robert Tisserand and Rodney Young.  ISBN 978-0-4430-6241-4.

(Wow, its jumped $20 since I bought it just before Thanksgiving - still well worth the price, IMO.  Also available on Amazon.)

Chapter 13 contains an alphabetized list of ~400 EOs (incl some absolutes) and gives their compositions as determined by GC-MS, and chapter 14 is an alternative way of organizing this info - its an alphabetized list of individual chemical compounds, with lists of the EOs in which they are found (and approx compositional ranges).

I also recently watched some YouTube videos on EO Chem, recorded from live classes given at Indiana U.  For those with a chemistry background, the videos can move slowly at times.  Once he gets into the different compounds it gets interesting.  Good way to kill a rainy Sunday.


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## Saponista (Dec 6, 2015)

Thanks Dr.j I will have a look


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## Arimara (Dec 6, 2015)

I'll have to buy the book after the holidays are over. I have _The Green Pharmacy Herbal Handbook_ and since my late teens/early twenties, it's been one of my favorite references.


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