Dihydrocoumarin

[jfrater]

Hi all,

Can anyone tell me the main difference between coumarin and dihydrocoumarin and why you might use one over the other? I have natural coumarin and am just waiting on a sample of natural dihydrocoumarin so I can do a comparison but I'm curious about other's experiences.

 

[Chris Smith]

I read on the net that unlike coumarin, dihydrocoumarin causes skin sensitization. And, dihydrocoumarin shouldn't be used as a fragrance ingredient, according to the IFRA. Dihydrocoumarin has an odor similar to coumarin at room temperature or reminiscent of nitrobenzene at higher temperature. Apparently dihydrocoumarin is derived from the metabolism of coumarin by s. cerevisiae.

 

[jfrater]

I read on the net that unlike coumarin, dihydrocoumarin causes skin sensitization. And, dihydrocoumarin shouldn't be used as a fragrance ingredient, according to the IFRA. Dihydrocoumarin has an odor similar to coumarin at room temperature or reminiscent of nitrobenzene at higher temperature. Apparently dihydrocoumarin is derived from the metabolism of coumarin by s. cerevisiae.

I am not concerned about IFRA. Is there a difference in the fragrance is what I care about In the past why would one use dihydrocoumarin over coumarin?

 

[Chris Smith]

I'm not sure, but I'm guessing that dihydrocoumarin was valued as a fixative.

 

[jzainoun]

Coumarin smells stronger to me


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[edshepp]

To my nose, dihydrocoumarin smells a little more spicy and maybe richer than coumarin. Not as powdery as coumarin. I get more of a tonka impression from it, one that I don't get from coumarin or octahydrocoumarin.

 

[David Ruskin]

I have always understood that Dihydrocoumarin was used in Flavours (whilst Coumarin could not be used), and vice versa; Coumarin in Fragrances, Djhydrocoumarin not.

 

[jfrater]

Ah that's very interesting David and may answer my other question relating to my GCMS results! I am guessing the library used to analyse the results is primarily used for flavor analysis so it reported dhc because it is probably chemically similar to coumarin.

 

[David Ruskin]

Could well be; makes sense.

 

[DeletedUser20210620]

Bo Jensen says this about Tonka Bean, Coumarin, Dihydrocoumarin:

Tonka beans
Dipteryx odorata (Fabaceae)
The seeds from the large tree Dipteryx odorata growing in northern South America are called tonka beans. They contain coumarin in the form of a glycoside. When the seeds are fermented, coumarin is liberated in substantial amounts, often forming an "icing" of crystals on the surface. Coumarin was isolated and identified from this natural source as early as in 1820. A tonka bean absolute is obtained by extraction of the seeds. It is used in perfumery and in the flavouring of tobacco. It is a semi-solid or crystalline mass of pale amber or pale brownish-yellow colour. The odour is very rich, sweet and warm, distinctly coumarinic-herbaceous, with a prune-like or caramellic-sweet undertone. The absolute consists of 20-45 % coumarin, but the effect goes far beyond that of the coumarin contained in the absolute - according to Arctander (see end of references). Minor components like dihydrocoumarin (with a sweet-herbal odor), 5-hydroxymethyl-furfural (with a cinnamon- and dried fruit-like odor) and methyl melilotate contribute to the unique tonka bean aroma [316] [317]. Recently, tonka beans have appeared as a new "exotic" spice in fashion cuisine. However, coumarin is toxic by intake in more than minute amounts - see below!
Etymology: In the local Tupi language the tree is called Tonka or Coumarou.
about new artificial coumarinic odorants
Coumarin occurs in several plants and is an example of a secondary metabolite with allelopathic properties, i.e. it inhibits the growth of competing species. Moreover, coumarin is toxic to rodents (causing internal hemorrhage). It is moderately toxic to humans (by intake) but the risk from cosmetic use is still disputed. It is banned as a food additive in numerous countries. However, some natural food additives containing coumarin (woodruff and bison grass, for example) are allowed for special purposes. From a perfumery viewpoint, alternatives are of interest, also for variations of the coumarin theme. A few examples:

Coumane ®, a cyclopropane analogue of coumarin from Flexitral, has just received FEMA GRAS status for use as a flavor. The odor is said to be strikingly close to that of coumarin.

Octahydrocoumarin, marketed by IFF as Bicyclo Nonalactone, has a heavier and more coconut-like odor than that of coumarin.

Methyl Laitone ® (Givaudan) is an extremely powerful odorant with a diffusive, milky, coconut-like coumarinic character.

Cantryl ® (Symrise) surprises being a nitrile with a powerful, cumin-shaded coumarinic sweetness. Cantryl is announced as "coumarin's radiant sister"!
Etymology: Cantryl, from campholenic acid nitrile.

 

[DeletedUser20210620]

http://www.bojensen.net/EssentialOilsEng/EssentialOils29/EssentialOils29.htm#Tonka

 

[jfrater]

Thanks Rick - that's a really useful site I find. I have actually cooked with tonka bean - it is quite popular in French pastry cuisine at the moment in creams and fillings. The beans have the most beautiful odour.

As for my original question, the amount of dihydrocoumarin (which is probably coumarin due to a GCMS error) is quite high (4% of the juice) so I suspect it is definitely coumarin that was used and not tonka bean.

 

[DeletedUser20210620]

Thanks Rick - that's a really useful site I find. I have actually cooked with tonka bean - it is quite popular in French pastry cuisine at the moment in creams and fillings. The beans have the most beautiful odour.

As for my original question, the amount of dihydrocoumarin (which is probably coumarin due to a GCMS error) is quite high (4% of the juice) so I suspect it is definitely coumarin that was used and not tonka bean.

I know, i have almost 1kg of tonka with me to do a tincture I keep smelling the box, the aroma is gorgeous.

Are you sure that your natural coumarin comes from dipteryx odorata? If the came from Brazil or another South American country, it might also be a tree called amburana cearensis that has seed with similar aromachemicals to the one in dipteryx odorata...

Or maybe the soil and environment configuration influences the amounts of each chemical? Just guessing....

 

[Chris Smith]

Wow, I wish I had a box of Tonka -- I'm jealous! Speaking of Brazil, I also wish I had a perfumery material from the Clethra alnifolia, which has a heliotrope characteristic. I smelled this last weekend while canoeing in NJ's Pine Barrens (on the Great Egg Harbor River). It grows along with blueberry on the river banks (yes, I did eat the blueberries!).

 

[DeletedUser20210620]

Wow, I wish I had a box of Tonka -- I'm jealous! Speaking of Brazil, I also wish I had a perfumery material from the Clethra alnifolia, which has a heliotrope characteristic. I smelled this last weekend while canoeing in NJ's Pine Barrens (on the Great Egg Harbor River). It grows along with blueberry on the river banks (yes, I did eat the blueberries!).

Chris, i couldn't find any reference to it procuded here in Brazil, aren't you sure it's a relative to this plant?

One that is not from here but it's from south america and it's lovely is Paramela (Adesmia Boronioides). Concentrated smells like leather and has an animalic nuance, but diluted at 10% has a green flowery aroma and tea nuances. Quite expensive, but very lovely.

 

[jfrater]

I know, i have almost 1kg of tonka with me to do a tincture I keep smelling the box, the aroma is gorgeous.

Are you sure that your natural coumarin comes from dipteryx odorata? If the came from Brazil or another South American country, it might also be a tree called amburana cearensis that has seed with similar aromachemicals to the one in dipteryx odorata...

Or maybe the soil and environment configuration influences the amounts of each chemical? Just guessing....

I didn't create the original fragrance - I am guessing they used coumarin rather than tonka bean. It's a 1920s scent and while tonka was still used them coumarin was also available and popular.

 

[Chris Smith]

Hi rickbr, I don't know if they've actually been able to make a fragrant extract from the flowers. But, Clethra is the name of a fragrance or perfume available for sale in Brasil. Perhaps it's just a composition inspired by the scent of the flowers. I can tell you that while canoeing down the river, this scent permeated the air. I was astounded by it and very curious at to what it was! Later, I found out through a Google search that it was Clethra. Here in New Jersey, USA, you can only have this experience at this time of the year, when it blooms. But, you can definitely find it in Brasil too (although it isn't found everywhere). The fragrance is very inspirational for a perfumer

 

[DeletedUser20210620]

I didn't create the original fragrance - I am guessing they used coumarin rather than tonka bean. It's a 1920s scent and while tonka was still used them coumarin was also available and popular.

I thought that you were comparing to some gc-ms analysis of tonka beans

 

[DeletedUser20210620]

Hi rickbr, I don't know if they've actually been able to make a fragrant extract from the flowers. But, Clethra is the name of a fragrance or perfume available for sale in Brasil. Perhaps it's just a composition inspired by the scent of the flowers. I can tell you that while canoeing down the river, this scent permeated the air. I was astounded by it and very curious at to what it was! Later, I found out through a Google search that it was Clethra. Here in New Jersey, USA, you can only have this experience at this time of the year, when it blooms. But, you can definitely find it in Brasil too (although it isn't found everywhere). The fragrance is very inspirational for a perfumer

Oh, i found it. The brand that sells it is famous for doing mainstream dupes for very reasonable prices. The curious is that they usually are very close to the creation they are cloning.I believe this one is a Lady Million copy, i doubt they knew there was a plant with that name and smell lol
Your description about Clethra makes it very interesting! Maybe it's possible of extracting the aroma?

 

[Chris Smith]

Hi rickbr, Yes... I saw it on the net as well and the packaging did look suspiciously 'cheap'. I keep searching the net, but so far I can't find any extract of Clethera. It's known as Sweet Pepperbush, Anne Bidwell, Summersweet, 'Sixteen Candles', Coastal White Adler, etc.

 

[salmanalfatih56]

I prefer to use 6-methylcoumarin aka toncarin in my perfume formula😎