Citral

Citral, or 3,7-dimethyl-2,6-octadienal or lemonal is either a pair, or a mixture of terpenoids with the molecular formula C₁₀H₁₆O. The two compounds are double bond isomers. The E-isomer is known as geranial or citral A or transCitral. The Z-isomer is known as neral or citral B or cisCitral…. 

I assume, it is the most boring entrance ever… (Wiki style J )

Let me use my own words;

Citral consists of 2 BFF, ¡Best Friends Forever!, Geranial & Neral. Besides they are best friends, they are also monozygotic twins (identical formula, C10H16O) with different attitudes. Geranial is more aggressive than Neral. When Geranial gives strong fresh lemon odor, his twin brother Neral gives the same lemon odor but not that strong but also sweeter.

Citral is a pale yellow liquid. It is less dense than water (0.9 g/cm3) and not soluble in water neither but only in alcohol and some other solvents.  

Want some citrusy taste or odor? Citral is your buddy..

USAGE of CITRAL

Citral is used directly in Fragrance and Flavor (F&F) industry or as a starting material to produce Menthol, Aroma Chemicals and Vitamins (A&E).  

Direct usage;

Citral is often used to give a citrusy zing to fragrances and a citrus flavoring to sweets and soft drinks.

It’s also used when imitating grapefruit, orange, lime and even to give the fresh fruit tang to apple and strawberry products.

Similarly, the fragrances used in producing perfumes and soap will often include citral in everything from oil of bergamot to ginger and rose. If you use laundry, dishwashing products or cleaning products with a lemon scent, they probably have Citral.

All Fragrance and Flavor (F&F) houses use a lot of Citral in their formulas.

Starting Material;

Citral is used as a starting material to produce many important Aroma chemicals, Menthol and also Vitamin A and E.

Some aroma chemicals derived from Citral à Citronellol, Citronellal, Geraniol, Hydroxycitronellal, Beta ionone, Linalool, Linalyl Acetate, Rose Oxide, Citronellyl acetate, Geranyl Acetate, Pyranol ….

Also if you consider the derivatives of these aroma chemicals, it would be easier to understand how important Citral is for F&F world.

For those who likes graphs, come here! Here you see usage of Citral.

 

Right now, stop what you are doing, which is reading.. well okay, dont stop what you are doing, but stop what you are thinking and think about Citral and give her a "salud", because the taste of Mint that refreshes you right now with a gum in your mouth is from this magical ingredient. 

                                          << Salud >>

Menthol Synthetic. And this is not my hand! 

SOURCING CITRAL

There are two source of Citral. Naturally sourced Citral and synthetically sourced Citral.

Citral Natural

You see below Natural sources and citral contents of them

Source	Plant Origin	Citral Content %
Lemon Myrtle	Australia	90-98
Lemon Grass	India, Adrica, South East Asia	65-85
Litsea Cubea	China, Indonesia, South East Asia	70-85
Lemon Tea-Tree	Kenya, South Africa, Australia	70-80
Clove Basil	Africa, Southern Asia	65-70
Petitgrain	Paraguay, France	35-40
Lemon Verbena	South America	30-35

As you see in the graph, LEMON MYRTLE has the highest content of Citral where LEMON GRASS and LITSEA CUBEBA are the most common source for Citral Natural.

Citral from Lemon Grass 

Litsea Cubeba with 70-85 % Citral 

Citral Synthetic

Before talking about Citral synthetic, I believe I should dig the history of Citral a little to understand WHY on earth we needed synthetic Citral? Isnt Naturally sourced Citral enough or what?  

Vitamin A (I can see empty eyes when I started with Vitamin A suddenly but I promise there is a connection) is essential for human development, the support of immune system, gene transcription, skin and cellular health, effective vision (eyes, not mental vision! You should travel for thatJ) etc. etc.

Carrot is healthy!

Vitamin A was produced first in 1947 by two Dutch scientists by reacting Citral with Acetone to form Beta-ionone which is further processed to synthesize Vitamin compounds.

In this process, to produce Vitamin A;

Citral is an important intermediate and become much more important and needed.

ATTENTION!!! we are talking about 1950`s, right after 2^nd world war, half of the population was wounded, people need to be treated and developed physically. So the demand on these kind of supplementary increased a lot.

Plus naturally sourced Citral was being used for perfumery already.

On top of it, it was hard to get the consistency of quality required for medical use

So here is where we NEED more and Medical quality Citral!!!

As a result, the chemical company Roche found an alternative route to beta-ionone, while competitor BASF produced Citral instead, from readily available Isobutene and Formaldehyde (Petrochemicals). BASF remains one of the world’s biggest producers of Vitamin A and Citral right now!

How sad for Roche no? If they focus on producing Citral instead of Beta Ionone, they would be the one who says “we create chemistry” now JJ

At the end we can separate Citral History into 2 era, BVa (before Vitamin A) and AVa (after Vitamin A) J

BASF developed very complicated and sophisticated process to synthesize Citral from the reaction of ISOBUTYLENE and FORMALDEHYDE which can be shown as below;

Yes this is my finger..

Well ok, agreeJ, it does not seen that complicated in my hand-made drawing but believe me it is super-complicated!!

At the end, thanks to BASF, today we are able to produce Citral synthetic and leave alone a little bit these cute and beautiful Lemon Grass or Litsea Cubeba bushes.. 

INTERESTING FACTS

Like Citronela Oil, citral has an effect on some insects. It has a mild repellent action for some species, but for bees the effect is quite the opposite. J

Citral is a component of the Nasanov pheromone, produced by worker bees to help foragers (bees for finding food) find their way back to the hive. Citral, on its own, attracts foraging honey bees and can be used by beekeepers to bring them to a particular location. It is kinda catnip for cats J

Citral has a very special effects on another animal. It also appears to act as a sex pheromone for the green-veined white butterfly, released by males to attract mates. Its Channel Bleu of green-veined white butterfly when they hunt JJ

Also two studies have shown 1–1.7% of people to be allergic to Citral 

" himmm would you like some Citral honey-bee ?? "

Ylang Ylang Oil

If you define essential oils as a mimic on a child face, a warm, happy and innocent smile would go for Ylang Ylang oil definitely! 

Warm, soft, relax and divine are some of the expressions come to my mind when I sniff deep the scent of Ylang Ylang oil.


YLang Ylang oil is another essential ingredients in fragrance industry. 
It is used to provide depth to the heart of the perfumes along with sweet and floral accords, yet a bit earthy, peppery and creaminess. 
When you check the iconic best seller floral perfumes in fragrance history, you always see Ylang Ylang oil on top of the formula. 
Such as Chanel No.5, Valentino, Poison, L'air du Temps, Diorrissimo ... 

It is so pure, smooth and full of passion that you can feel nature's femininity in this beautiful oil. 

Ylang ylang  originated in the Philippines and name comes from Filipino word Alang-Ilang, which means  the lightness and the mobility of the flower to the least breath of wind... WOoOooW right!!   

However many people believes that the meaning of its name is flower of flowers

Ylang ylang oil is obtained by steam distillation of flowers of Cananga Odorata tree which belongs to Annonaceae family.

Cananga odorata is a fast growing tree that can reach up to 30 mt height in its 25 years of flower-producing life. Lucky for us that blooming is all year round and the tree yields a large amount of flowers. 
That much active tree is needed to be under control of course ✋ Hence extensive pruning is very essential to restrict this fast growing and also leads tree to produce more flowers. 

A tree that is more than 5 years old gives 20-25 kg of flowers per year!!
To produce 1-1,5 Kg Ylang Ylang oil, 50 kg of flower is needed to be distilled.. 

So if you have 2 Cananga Odorata trees in your backyard and a little distillation unit at home, you can have 1 kg of Ylang Ylang oil per year by only following its flowering period. AWESOME!!

To stand under a ylang ylang tree is to inhale peace and serenity

So what about this flower 

which gives us the most valuable thing it has.. 

Star-Shaped flowers are so delicate and shy that they must be collected by hand at dawn and sent to the distillation immediately !! (in 2 hours max).

Harvesting in very early morning is necessary as the flowers accumulate the maximum amount of essential oil during the night. On the contrary during the day with open sun oil rapidly diminishes. 

The best flower is long and narrow six petals with a fresh and alive greenish yellow color and a pinkish red center 

The main flowering seasons are immediately after rain and during the dry season
• Low flowering periods in December - March and July – September
• High flowering in April - July and in October - December. 

A picker, the ones should be taken care of and deeply appreciated, can collect 20-25 kg of flowers per day. 

WHERE

Madagascar, Mayotte and Comoros are the main supplier of YLang Ylang oil. Comoros with 55-65 MT capacity is the dominant global source of this oil especially on little island called Anjouan where homes of more than 350 small distillers. 

Due to high labor cost in Mayotte, Ylang Ylang oil production has dropped dramatically in recent years and shifted to Madagascar. 
Remember! Early picking is necessary thus labor force is quite hard thing to supply and in many towns it is very expensive. 
   

Annual global production is around 90-110 MT and we can order geographically as follows:

  Comoros     55-65 MT

Madagascar  30-35 MT

Mayotte     1-5 MT

TEChNIC

Ok let me blow your mind with some super-boring yet helpful Technics about Ylang Ylang Oil .) 

But warning! It takes some time to read and not very fun as above, so before starting just click this to turn some music on..

Ok here we go!

Ylang-ylang essential oil production has the particularity of relying on a fractionation, based on distillation times, resulting in four to five grades of oil that have different commercial applications. (💥 I can see your face after this sentence)

Which means that YLang YLang oil has 4-5 different grades (depending on the distiller) with different qualities comes from different fractions of the steam distillation. 

We can see table below the fractions of Ylang Ylang Oil according to fraction times; 

Super Extra Ylang First half hour
Extra Ylang                    1st hour
Premiere   (Ylang – 1) 3rd hour
Deuxieme (Ylang – 2) Up to 5th hour
Troisieme  (Ylang – 3) 8 to 15 hour


These grades are also determined by the Spesific Density (SG) of the oil. 

Specific density can be a parameter that shows the quality of Ylang Ylang Oil. First fractions has bigger SG where the late fractions have smaller value. 

But what makes SG bigger? Another saying is what gives Ylang Ylang oil value? Answer is simple; Soil quality, climate, raining periods, wind, sun, water etc. which is basically Nature!

As we mentioned previously that Comoros is the dominant main supplier of the world, also Comoros is the dominant supplier of PREMIER quality of Ylang Ylang Oil thanks to its Nature.

Ok check this out. You will see better with this table. 
Here is a list for Grades(quality) x Specific Density x Origin 

                                     SG              Comoros % Madagascar %
Extra & Extra Super 950 – 970                 24                  3
Premiere                   935 – 945                 10                  20
Deuxieme                  920 – 935                 8                   17
Troisieme                  900 – 920                58                  60

As you see in the table, you get 24% Extra and Super extra quality of Ylang oil during the first fraction in Comoros where you get only 3% in Madagascar. That’s why Comoros is quite important for little island for high end perfumery industry.  

Ok lets go deeper!! 👍

These grades of Ylang Ylang Oil has different odor type comes from different chemical compositions of course, the first fraction being richer in very volatile compounds like esters, aldehydes or alcohols, while the last fractions are richer in less volatile compounds like sesquiterpenes. 

DEEPER, DEEPER!!

First fractions of Ylang Ylang Oil (Super Extra and Extra quality) is rich in the characteristic components of Ylang Ylang which can be listed as p-Cresyl Methyl Ether, Methyl Benzoate, Linalool, Benzyl Acetate and Geranyl Acetate.
When the fraction continuous (Ylang-1, 2 or 3) contents of these components significantly reduce. 

For example, you find around 9% of p-cresyl methyl ether in Ylang Ylang Extra quality where you find only 0,5% in Ylang -3 or Linalool around 11% in Ylang Extra but around 2% in YLang - 3 

As you see fractions has completely different odor types due to different chemical compositions. 

If you still have energy to read more, I have more things to write! Camon lets go deeper!!..
With music of course. :)

Lets have a look at the components and their odor effect on Ylang Ylang Oil;

Esters 

This class of chemicals is very important to the odor of Ylang. 
Methyl benzoate is without a doubt the most characteristic chemical and is responsible for the odor most identical as Ylang. 
Benzyl Acetate and Geranyl Acetate provide the fruity floral body of Ylang.
Methyl Salicylate and Benzyl Salicylate are phenol esters and provide firstly a bright floral medicinal note and in the later a long lasting floral body. 

Ethers 

The major component in this class is p-cresyl methyl ether. It is responsible for the very diffusive and penetrating medicinal character of Ylang.

Alcohols 

The major alcohol in this group is Linalool. 
The character of Iinalool is giving bright, splash citrus and floral notes. 
While there are other familiar floral alcohols, such as Benzyl alcohol, Alpha terpineol, Geraniol, Farnesol and Nerolidol, however their part in the overall odor of Ylang is minor.

Phenols

This class of chemicals almost always plays an important part in the odor profile of any natural products!! Usually they are in trace quantities, their presence is felt from top note to base note. Ylang is a perfect example of how these phenols, such as p-Cresol, Eugenol, Isoeugenol and 2-methoxy-4-methyl phenol, make their presence felt in just that way. 
They are responsible for the spicy, warm balsamic effect for which Ylang is so well known.

Aldehydes 

Benzaldehyde and Furfural are two very important aldehydes with very characteristic odors. They contribute to the fruity character of Ylang.

Hydrocarbons

The sesquiterpene hydrocarbons comprise approximately 40% of Ylang!! 
Ups, Helloouuu… The sesquiterpenes as a class, specifically Caryophyllene and Cadinene, can generally be described as woody and more or less peppery note supplyer to our valuable Ylang Oil. 

That’s it! Done! Enough technics I assume!!

Mother Nature loves us, and it shows in many ways. For me, Ylang Ylang Oil is one of the way that shows perfectly how she offer and share the most beautiful treasure of her generously. 

Please Care and Respect Nature and Love Ylang Ylang oil 😊

No it is Just a smile :)