Direction Lemon acorrd

[DruidHR]

Hello,

I hope this is the good forum to post this question.

I'm in loved with "citrus" accords from these two perfumes:

• Chanel allure homme edition blanche
• Chanel allure homme sport cologne

I searched about Lemon/Citrus accords on this forum, but there are a lot of different types of formula for Lemon/Citrus accords.
Can anyone point me in right direction about those accords. Any hint about ingredients list or post on this forum would be great.

Are info about ingredients from notino, parfumo.net and fragnatica.com any good?

Thanks in advance

 

[parker25mv]

Really simple answer:
By far the most important piece of the smell of lemon is citral. It kind of smells like lemon drop candies, maybe a little reminiscent of lemon sorbet. It has a kind of transparent feel, only slightly opaque or semi-translucent, like a sorbet, or maybe light delicate freshly fallen snow. It smells very fresh and diffusive.
Next comes limonene, and in lemon that is mainly L-limonene, but it also contains a little D-limonene. L-limonene is more sour and reminds one of lemon-scented Pine-Sol. It is a dry woody smell, maybe distantly reminiscent of turpentine. D-limonene smells much more tangy and orange-like, or more specifically the little oil glands in the peel of mandarin orange. If you have ever smelled pine needles and smelled something a little orange-like, that is from D-limonene.
Lemon also contains a little bit of ionones. This occurs at extremely low levels because it is very potent in effect. Ionones smell reminiscent of violets, but at low levels add a brightness, radiance, life, and diffusion, maybe described as a "powdery" feeling.
Those are the three main and most important ones, but there are several others that occur in smaller amounts or are of lesser importance in lemon.

A good starting point for a lemon accord is maybe 38 to 55 percent limonene, between 4 to 9 percent citral, 0.4 percent ionone.
But realise that IFRA places a maximum allowable limit of 0.6 percent citral in the final fragrance concentrate for perfumes. And it's usually a good idea to put a tiny amount of BHT or tocopherol in anything with lots of limonene, maybe 0.1 percent.

Actually a good place to start for a lemon accord is to use actual lemon oil and then reinforce it by adding small amounts of other things, mainly citral. You don't have to add limonene if the accord uses lemon oil as a main base.

It's also common in perfumery to use an AC such a Lemonile, to overcome the restrictions on citral (and because its smell will not degrade). Lemonile is very similar in effect to citral, but doesn't quite smell as good, is a little bit metallic smelling, and is several times stronger smelling than citral.

C-9 aldehyde can help reinforce the citral, adding a citrus juiciness effect and more diffusion and sparkle. It will add kind of an "oily" feel and be waxy, reminiscent of how fresh rose petals can smell a little waxy. Maybe use at 2 or 3 percent in an accord (lower if the final fragrance is completely dominated by lemon). C-9 is probably the most "lemon"-like of the simple straight chain aldehydes; not that it really smells like lemon; it just has a little lemon-reminiscent vague sourness in its character.

The AC Florol can also be a good one to add, at maybe 2%. Linalool is pretty common to add as well, maybe 3 to 5%. Perhaps Fenchol, 1.5%, or Prismantol, 0.8%.

You can experiment with some citronellol (maybe 2-3%), or if you're looking for something more refined (and expensive), Rhodinol 70, has kind of a sharp lemony wildflower in a mountain meadow feel. or try lemon grass essential oil in your accord too, if you want. For some reason it does not seem to be that commonly used by perfumers but nerol is one to consider (adding some sophisticated complexity and soft citrus texture, nice smelling; it's less "yellow lemon" in character than citronellol yet in another way sort of reminiscent of lemon, even almost slightly sweet, maybe reminiscent of geraniol but more mild and citrus-like).
If you're trying to go in a slightly more fruity floral direction, maybe linalyl acetate. And then C-9 aldehyde to help add juiciness.

 

[pkiler]

For a citrus accord similar to Chanel Allure Homme, Start with Dihydromyrcenol : Bergamot EO : Lemon EO, at 9:5:4.

 

[chyprefresh]

Lemon also contains a little bit of ionones. This occurs at extremely low levels because it is very potent in effect. Ionones smell reminiscent of violets, but at low levels add a brightness, radiance, life, and diffusion, maybe described as a "powdery" feeling.

Gamma terpinene is a pretty important one to add for lemon that you overlooked along with beta pinene, the citral content should be lower than 7%, more like 1-2%. And what ionone(s)? I don't see anything like this in my gcs...

 

[parker25mv]

the citral content should be lower than 7%, more like 1-2%.

In the entire fragrance, or rather fragrance concentrate, yes. But if we are talking about a lemon accord that will be mixed in and added to the rest of the fragrance, it's a different matter.

It's rather difficult, nearly impossible, to make a 100% lemon accord that meets IFRA restrictions. Well, at least if you want a fragrance that is as strong as normal perfume.

You can have different personal views on this, of course. But the simple fact of the matter is citral is where the lemon smell comes from.

I fully agree that you should not be using 9% citral in the fragrance concentrate for the final fragrance. (Well, of course not unless the fragrance concentrate is going to be diluted in perfumer's alcohol down far more than normal)

One study found the dermal sensitisation threshold for citral was 1400 micrograms/cm2.
(Citral: Identifying a threshold for induction of dermal sensitization, John Lalko, Regulatory Toxicology and Pharmacology 52(1):62-73, February 2008 )
For comparison, linalool is 13793 micrograms/cm2, suggesting citral is nearly 10 times more sensitising to skin.
The recommended maximum level of linalool in a fragrance (fragrance concentrate) is 4.3%, although IFRA does not seem to set an official limit. Certain sensitive people may be more likely to have a skin reaction at that level.

You can start to see why there are not many fine fragrances with a very strong lemon note, or why many fragrance formulas that want a very strong lemon note resort to Citralva or Lemonile instead, even though the smell necessarily becomes somewhat metallic.

I know there are going to be some of you who are extremely skeptical, so I'll explain it this way. Take some other non-lemon fragrance and start adding citral to it. What percentage of citral do you have to add until the lemon note dominates over the rest of the fragrance? Until it becomes mostly a lemon fragrance.

Since we are talking about a lemon accord, in some sense I do believe it is kind of meaningless to talk about trying to restrict the citral to a certain level, unless you also want to use a large percentage of something non-smelling like perfumer's alcohol or DPG in the accord, which is kind of absurd.

 

[DruidHR]

For a citrus accord similar to Chanel Allure Homme, Start with Dihydromyrcenol : Bergamot EO : Lemon EO, at 9:5:4.

Thx for the advice.

What about adding citral, limonene, etc... to these three?

 

[DruidHR]

Really simple answer:
By far the most important piece of the smell of lemon is citral. It kind of smells like lemon drop candies, maybe a little reminiscent of lemon sorbet. It has a kind of transparent feel, only slightly opaque or semi-translucent, like a sorbet, or maybe light delicate freshly fallen snow. It smells very fresh and diffusive.
Next comes limonene, and in lemon that is mainly L-limonene, but it also contains a little D-limonene. L-limonene is more sour and reminds one of lemon-scented Pine-Sol. It is a dry woody smell, maybe distantly reminiscent of turpentine. D-limonene smells much more tangy and orange-like, or more specifically the little oil glands in the peel of mandarin orange. If you have ever smelled pine needles and smelled something a little orange-like, that is from D-limonene.
Lemon also contains a little bit of ionones. This occurs at extremely low levels because it is very potent in effect. Ionones smell reminiscent of violets, but at low levels add a brightness, radiance, life, and diffusion, maybe described as a "powdery" feeling.
Those are the three main and most important ones, but there are several others that occur in smaller amounts or are of lesser importance in lemon.

A good starting point for a lemon accord is maybe 38 to 55 percent limonene, between 4 to 9 percent citral, 0.4 percent ionone.
But realise that IFRA places a maximum allowable limit of 0.6 percent citral in the final fragrance concentrate for perfumes. And it's usually a good idea to put a tiny amount of BHT or tocopherol in anything with lots of limonene, maybe 0.1 percent.

Actually a good place to start for a lemon accord is to use actual lemon oil and then reinforce it by adding small amounts of other things, mainly citral. You don't have to add limonene if the accord uses lemon oil as a main base.

It's also common in perfumery to use an AC such a Lemonile, to overcome the restrictions on citral (and because its smell will not degrade). Lemonile is very similar in effect to citral, but doesn't quite smell as good, is a little bit metallic smelling, and is several times stronger smelling than citral.

C-9 aldehyde can help reinforce the citral, adding a citrus juiciness effect and more diffusion and sparkle. It will add kind of an "oily" feel and be waxy, reminiscent of how fresh rose petals can smell a little waxy. Maybe use at 2 or 3 percent in an accord (lower if the final fragrance is completely dominated by lemon). C-9 is probably the most "lemon"-like of the simple straight chain aldehydes; not that it really smells like lemon; it just has a little lemon-reminiscent vague sourness in its character.

The AC Florol can also be a good one to add, at maybe 2%. Linalool is pretty common to add as well, maybe 3 to 5%. Perhaps Fenchol, 1.5%, or Prismantol, 0.8%.

You can experiment with some citronellol (maybe 2-3%), or if you're looking for something more refined (and expensive), Rhodinol 70, has kind of a sharp lemony wildflower in a mountain meadow feel. or try lemon grass essential oil in your accord too, if you want. For some reason it does not seem to be that commonly used by perfumers but nerol is one to consider (adding some sophisticated complexity and soft citrus texture, nice smelling; it's less "yellow lemon" in character than citronellol yet in another way sort of reminiscent of lemon, even almost slightly sweet, maybe reminiscent of geraniol but more mild and citrus-like).
If you're trying to go in a slightly more fruity floral direction, maybe linalyl acetate. And then C-9 aldehyde to help add juiciness.

Thx for the advice.

I'll start playing with those ingredients and try to find what I whant.

What about aldehyde C-10 decanal? I read that it is recommended to use it in citrus accords or in final fragrances.

 

[parker25mv]

What about aldehyde C-10 decanal?

Sure, of course you could use it, and the two smell pretty similar overall, but be aware that C-9 does have somewhat of a more sour lemon character than C-10, whereas C-10 leans a little more on the side of mandarin orange in character. With citral in there, it probably won't matter, but every ingredient can play a role in helping to push it towards a more specific lemon character rather than citrus in general. It's hard to describe exactly how these aldehydes smell; they are kind of reminiscent of the waxy surface part of a citrus peel.

If for some reason you were trying to keep the citral to an absolute minimum, then it might be more important to choose C-9.

 

[DruidHR]

Sure, of course you could use it, and the two smell pretty similar overall, but be aware that C-9 does have somewhat of a more sour lemon character than C-10, whereas C-10 leans a little more on the side of mandarin orange in character. With citral in there, it probably won't matter, but every ingredient can play a role in helping to push it towards a more specific lemon character rather than citrus in general. It's hard to describe exactly how these aldehydes smell; they are kind of reminiscent of the waxy surface part of a citrus peel.

If for some reason you were trying to keep the citral to an absolute minimum, then it might be more important to choose C-9.

Thx

Already bought aldehyde C-10 but next month when budget is replenished I'll most definitely buy C-9 to.

 

[mnitabach]

Sure, of course you could use it, and the two smell pretty similar overall, but be aware that C-9 does have somewhat of a more sour lemon character than C-10, whereas C-10 leans a little more on the side of mandarin orange in character. With citral in there, it probably won't matter, but every ingredient can play a role in helping to push it towards a more specific lemon character rather than citrus in general. It's hard to describe exactly how these aldehydes smell; they are kind of reminiscent of the waxy surface part of a citrus peel.

If for some reason you were trying to keep the citral to an absolute minimum, then it might be more important to choose C-9.

Can you give some examples of different doses of c9 & c10 you tried in particular lemon accord contexts & what the different effects you observed at those doses were?

 

[pkiler]

Thx for the advice.

What about adding citral, limonene, etc... to these three?

You specifically asked about Chanel Allure Homme, so that is the basis for my response, by reading a formula.
As you are the Perfumer, you are free to do anything that you wish, including disregarding everything that Parker told you.
Parker didn't answer your question. I did.

 

[DruidHR]

You specifically asked about Chanel Allure Homme, so that is the basis for my response, by reading a formula.
As you are the Perfumer, you are free to do anything that you wish, including disregarding everything that Parker told you.
Parker didn't answer your question. I did.

Thx for quick reply 🙂

I'm sorry if I said something wrong, but my intention was to ask in what direction should I go with those ingredients. There are other replies that include other ingredients and you said in first reply that I should start with those ingredients.

For a citrus accord similar to Chanel Allure Homme, Start with Dihydromyrcenol : Bergamot EO : Lemon EO, at 9:5:4.

So, I just wanted to ask should I go in direction of citral, limonene, etc... or in some other.

Problem is that all this is completely new for me and every information that is deferring from other informationa is confusing to me.

 

[parker25mv]

So, I just wanted to ask should I go in direction of citral, limonene, etc... or in some other.

Problem is that all this is completely new for me and every information that is deferring from other informationa is confusing to me.

It depends on what "type" of lemon note you want. There are different directions to go with lemon, somewhat different types of lemon. We obviously cannot tell you which lemon you want.
For the sake of convenience, you have decided that you would be okay with a lemon note that smells like Chanel allure homme. You may not realise it but in some ways that makes it even more difficult, since it is difficult to precisely copy an exact note in another perfume.
I have not smelled Chanel allue homme.

Things that are complicated can often be confusing.

The most important thing in a lemon note is going to be citral. But usually you are only going to want to use a very small amount due to possibility of skin sensitisation. (That is if you are not already using lemon oil, which naturally contains citral)

Then there is the possibility of substituting citral with Citralva or Lemonile, as already mentioned, which adds more complication. It's frequently done in commercial perfumes, but maybe that is too complicated for you to think about. [cautionary edit: Citralva has recently been banned by IFRA from use in perfumes or cosmetics, due to chromosomal genotoxicity concerns]

If you want to keep things extremely simple you could just follow pkiler's advice and, if you want, add a tiny amount of citral to that. Maybe 0.5%. (You could add it starting in 0.1% gradients until you reach the level that smells good)

 

[David Ruskin]

"Then there is the possibility of substituting citral with Citralva"

Citralva (aka Geranyl nitrile) is no longer used in perfumery. It was banned over ten yers ago due its carcinogenicity. Use citronellyl nitrile instead.

Lemon oil contains about 2.0% Citral, (which does indeed smell of Lemon) so it isn't a major component.

"Lemon also contains a little bit of ionones"

I have never heard that this is true, can you site a source for this?

 

[parker25mv]

"Lemon also contains a little bit of ionones"

I have never heard that this is true, can you site a source for this?

The volatile components in the peel oil from Japanese fingered citron (Citrus medica L. var. sarcodactylis Swingle) were analysed by GC–MS for the first time. The main components were limonene (47.8%), gamma-terpinene (32.1%), alpha-pinene (2.9%), alpha-pinene (2.7%), geranial (2.5%), myrcene (1.7%), neral (1.6%), terpinolene (1.4%) and gamma-thujene (1.33%). The peel oil was characterized by the smaller content of limonene and the larger content of beta-terpinene, geranial and neral. [...] The content of neral and geranial in typical lemon oil is about 2.8%. [...]
Beta-Ionone, one of the aroma volatile components, was responsible for the characteristic osmanthus-like odour of the fruit. [...] Beta-Ionone has a very low odour threshold value (7ng/L) and it is an important aroma component in osmanthus flower"
Volatile components in the peel oil from fingered citron (citrus medica L. var. sarcodactylis swingle), Haruyasu Shiota, March 1990, Flavour and Fragrance Journal
They're just referring to the Buddha's hand citron. I've smelled one, it smells pretty much like lemon, except perhaps just a little more clean and floral, just a little bit purer "yellow lemon" than ordinary lemon, with even less "orange" citrus quality.

"Beta-Ionone, although present in the peel oil at a low concentration, is thought to be responsible for the distinctive aroma of the Ethrog fruit."
The Essential Oils of Etrog (Citrus medica L. Var. ethrog Engl.) Aromatic Plants of the Holy Land and the Sinai, Part VI Zhenia and Alexander Fleisher, pages 377-379, Journal of Essential Oil Research, Volume 3, Issue 5, 1991.
They refer to the Etrog variety of citron.

Citron is the ancestor species of lemon.

Edit: managed to find this...
"β-Ionone was absent in the sweet orange and was present in trace in all the other juices."
Biochemical characterization of blood orange, sweet orange, lemon, bergamot and bitter orange, Phytochemistry, Volume 62, Issue 8, April 2003, pages 1283-1289

Ionone is not absolutely essential to the smell of lemon, but tiny amounts can help give it effects. I personally seem to detect traces of ionone in the smell of lemon (var. Eureka), sniffing the surface of a fresh lemon on a tree. Although this is just my nose perception and could be a little subjective.

Citralva (aka Geranyl nitrile) is no longer used in perfumery. It was banned over ten yers ago due its carcinogenicity. Use citronellyl nitrile instead.

Perfumers World appears to still sell it.

"Geranyl nitrile (CAS No. 5146-66-7) has reported cosmetic use in personal care products according to the European Chemicals Agency (ECHA)
Geranyl nitrile has reported domestic uses, including in: cleaning and washing agents; and polishes and waxes.
The chemicals in this group have been 'prohibited' for use in fragrances as stipulated in the 41st and 43rd Amendment of the IFRA Standard (IFRA). SC Johnson & Son, Inc. has restricted the use of the chemicals in fragrances (SC Johnson, 2015) [...]
Observation in humans: Geranyl nitrile at 12 % did not produce skin irritation in a 48-hour patch test in 25 human volunteers (Opdyke, 1974).
IMAP Group Assessment Report, Geranyl and neryl nitriles: Human health tier II assessment, Australia, 2020

 

[David Ruskin]

Thank you Parker. You mention a, very, atypical Citron to back up your claim about Lemon oils containing ionones. I have never come across a perfumery used lemon oil that contained ionones. But who am I against the might of Cut and Paste?

According to IFRA, Citralva is prohibited. Citralva was banned, not because of skin sensitisation, but because of a perceived carcinogenicity. Whether or not it is still sold is irrelevant. Whether or not its use in non-skin products is still permitted is also irrelevant to this topic. All I know is that more than ten years ago we were instructed not to use it. I think you recommending its use is somewhat irresponsible.

 

[parker25mv]

Thank you Parker. You mention a, very, atypical Citron to back up your claim about Lemon oils containing ionones.

I cited information about two different varieties of citron. That should strongly suggest it is probably true for all citrons.
(In case you were not aware, nearly all varieties of citrons are considered a single species and are not hybrids; this includes both varieties mentioned)

If the aroma of citron contains something, it is very reasonable to assume that lemon probably does as well, although perhaps in smaller amounts.
Citron genetics are what gives lemon its distinctive character different from other citrus varieties.

I have never come across a perfumery used lemon oil that contained ionones.

Fair enough. But even if ionones are never added specifically to a lemon accord, they very often get inadvertently added in the final perfume formula in which the lemon accord is used. I can't think of a fine perfume fragrance off hand that contains a lemon note but doesn't also contain ionone. They go together.

 

[David Ruskin]

I cited information about two different varieties of citron. That should strongly suggest it is probably true for all citrons.

Prove it. Prove that the lemon oils used in perfumery contain Ionones. Citron oils, whilst available, are rarely used in perfumery. When I was working we were shown samples of Citron oils from our main Citrus oils supplier, but even they said very little was produced, and what was, was mainly used for flavours.

Citron fruits are used during the Jewish festival of Sukkot.

 

[parker25mv]

Whether or not its use in non-skin products is still permitted is also irrelevant to this topic.

That's not necessarily completely true. Not everyone making fragrances is doing so to make a perfume or something that will be applied to skin.

I think you recommending its use is somewhat irresponsible.

That's technically not entirely true. If you read my first post carefully, I only "recommended" Lemonile.
I only mentioned Citralva in later posts. I'm not sure that it could really be said that I "recommended" using it. Just to be entirely fair...

 

[parker25mv]

Citralva (aka Geranyl nitrile) is no longer used in perfumery. It was banned over ten yers ago due its carcinogenicity. Use citronellyl nitrile instead.

There's some circumstantial evidence to suggest that citronellyl nitrile might possibly be problematic in the same way that geranyl nitrile is.

Comparative metabolism of geranyl nitrile and citronellyl nitrile in mouse, rat, and human hepatocytes, Raymond A. Kemper, 2006 June;34(6):1019-29.
Summary: They were not able to find a difference in quick elimination from the body between the two. That is the reason why the difference in toxicity between the two is believed (or assumed) to be.

The belief that citronellyl nitrile is not problematic seems to be based on only a single study, which does not seem to be very persuasive.
(They just fed mice 2g/kg bodyweight and then dissected them 48 hours later, and didn't see significant amounts of chromosomal aberration in the bone marrow, called a micronucleus assay)

One study found that citronellyl nitrile revealed positive results (that's a bad thing) in an in vitro chromosome aberration test but negative in an in vivo micronucleus assay. For comparison, dodecanitrile tested negative in both types of tests.
Evaluation of genotoxicity of nitrile fragrance ingredients using in vitro and in vivo assays, S. P. Bhatia, V. T. Politano, A. M. Api, Food Chem Toxicol . 2013 September;59:784-92.

It seems that, ironically, you might yourself be guilty of exactly what you accused me of.