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Posts Tagged ‘Vitamin C derivatives’

Vitamin C and Vitamin C derivatives

Saturday, May 28th, 2011

About Vitamin C (L-ascorbic acid)

Vitamin C (L-ascorbic acid) is one of the very few skin care ingredients that is supported by strong and reliable scientific research and evidence.

However, it is also one of the most difficult products to formulate with, because it is extremely unstable.

As soon as l-ascorbic acid is mixed with water it starts oxidizing. This makes the l-ascorbic acid ineffective and also dangerous, because oxidized L-ascorbic acid is a pro-oxidant which may increase the formation of free radicals.

So, the challenge has been to make stable L-ascorbic acid products, or to make l-ascorbic acid itself stable.

Currently there are three ways this has been done:

1. The Skinceuticals Vitamin C Plus Ferulic Acid + Vitamin E formulation: The Skinceuticals study and patent shows that Ferulic acid stabilizes L-ascorbic acid, and in a lab this is probably true. However, the reality is that by the time customers get their bottle of Skinceuticals C+E+Ferulic it has been sitting on the shelves for too long, and when they open their bottle the product has turned orange, which means the L-ascorbic has started oxidizing and has become pro-oxidant.

2. Anhydrous C: “Anyhydrous” means “without water,” and this is a great way to formulate with the unstable Vitamin C. Instead of dissolving the vitamin C powder in water, it is mixed and dispersed into a silicone gel. W hen the silicone is applied to the face it acts like a dermal patch. The l-ascorbic acid will slowly be dissolved by the natural moisture in the skin, and the L-ascorbic acid will then be absorbed into the skin.

3. Vitamin C derivatives: To improve the stability of vitamin C in skin care, scientists have been looking for alternative solutions. One of these has been to create Vitamin C derivatives. Usually these are made by combining ascorbic acid with other molecules. Examples of these are the water soluble Magnesium Ascorbyl Phosphate and the oil soluble Tetrahexyldecyl Ascorbate (which is also known as Ascorbyl Tetraisopalmitate)

Vitamin C derivatives

 

Magnesium Ascorbyl Phosphate (MAP)

MAPMagnesium Ascorbyl Phosphate is a water-soluble vitamin C derivative. Magnesium Ascorbyl Phosphate is not acidic so it does not irritate the skin and it is more stable than vitamin C.

Studies have shown that Magnesium Ascorbyl Phosphate is JUST as effective at boosting skin collagen synthesis as L-ascorbic acid.

Magnesium Ascorbyl Phosphate has proven to be an effective skin lightener, reducing hyperpigemnetation in some test subject.

Finally, studies have shown that Magnesium Ascorbyl Phosphate protects against UVB induced skin damage, such as inflammation and free radical formation, both duuring and after exposure to sunlight.

Even Magnesium Ascorbyl Phosphate is a lot more stable than L-ascorbic acid, it still degrades slowly when exposed to light and air.

Tetrahexyldecyl Ascorbate ( Ascorbyl Tetraisopalmitate)

Tetrahexyldecyl Ascorbate is the latest development in Vitamin C derivatives.

Tetrahexyldecyl Ascorbate is oil soluble, just like your skin, which means that it easily penetrates into the skin. It is not acidic and it does not require a low pH to get it to penetrate the skin so it does not sting. It is also stable in air and water for up to 18 months, which means it will work as an anti-oxidant long after you start using it.

Studies have shown that Tetrahexyldecyl Ascorbate is an effective skin care product. It effectively suppresses UVB-induced skin pigmentation, possibly through its anti-oxidative activity.

Tetrahexyldecyl Ascorbate also prevented UVA induced oxidative stress, and it boosted collagen synthesis.

 

Magnesium Ascorbyl Phosphate (MAP) References

Kameyama K, Sakai C, Kondoh S, Yonemoto K, Nishiyama S, Tagawa M, Murata T, Ohnuma T, Quigley J, Dorsky A, Bucks D, Blanock K. Inhibitory effect of magnesium L-ascorbyl-2-phosphate (VC-PMG) on melanogenesis in vitro and in vivo.

Geesin JC, Gordon JS, Berg RA. Regulation of collagen synthesis in human dermal fibroblasts by the sodium and magnesium salts of ascorbyl-2-phosphate.

Austria R, Semenzato A, Bettero A., Stability of vitamin C derivatives in solution and topical formulations.

Kobayashi S, Takehana M, Kanke M, Itoh S, Ogata E. Postadministration protective effect of magnesium-L-ascorbyl-phosphate on the development of UVB-induced cutaneous damage in mice.

Kobayashi S, Takehana M, Itoh S, Ogata E. Protective effect of magnesium-L-ascorbyl-2 phosphate against skin damage induced by UVB irradiation.

 

Tetrahexyldecyl Ascorbate ( Ascorbyl Tetraisopalmitate References

Xiao L, Kaneyasu K, Saitoh Y, Terashima Y, Kowata Y, Miwa N. Cytoprotective effects of the lipoidic-liquiform pro-vitamin C tetra-isopalmitoyl-ascorbate (VC-IP) against ultraviolet-A ray-induced injuries in human skin cells together with collagen retention, MMP inhibition and p53 gene repression.

Ochiai Y, Kaburagi S, Obayashi K, Ujiie N, Hashimoto S, Okano Y, Masaki H, Ichihashi M, Sakurai H. A new lipophilic pro-vitamin C, tetra-isopalmitoyl ascorbic acid (VC-IP), prevents UV-induced skin pigmentation through its anti-oxidative properties.

Fitzpatrick RE, Rostan EF. Double-blind, half-face study comparing topical vitamin C and vehicle for rejuvenation of photodamage.


Vitamin C and anti aging skin care products

Wednesday, January 20th, 2010

Without a doubt the most popular skin care products are those which use Vitamin C, also known as L-ascorbic acid.

In this post I will write about Cellex C and Skinceuticals C E Ferulic, two popular anti aging skin care products that use Vitamin C as their main active ingredients.

I will also discuss the problems with using Vitamin C in anti ageing skin care products and some other the alternatives that are available in the form of Vitamin C derivatives.

In the next post I will be giving some examples on how we can make our own DIY Cellex C and DIY Skinceuticals C E Ferulic products.

Vitamin C and anti-aging skin care

Vitamin C is one of the most popular ingredients in anti aging skin care products. Vitamin C can benefit the skin in two ways. First it can increase collagen production, and second as an antioxidant it can reduce and prevent skin damage caused by free radicals.

Vitamin C is also one of the most studied active ingredients in anti aging skin care. These studies examined the various ways in which Vitamin C increases collagen synthesis, and the way in which vitamin C prevents free radical damage, as well as UVB damage.

For more details about these studies, please look at this list of abstracts.

Cellex C

Commercial skin care products with vitamin C started with Cellex C. Developed by Lorraine Meisner , who is a cell biologist at UW-Madison, Cellex-C was quite revolutionary. There is an interesting article about her here.

From a DIY skin care point of view Cellex C is not very practical.  The three main ingredients are: L-ascorbic acid, the mineral zinc and the amino acid tyrosin.

Tyrosin has poor solubility in water and alcohol, and requires the use of some very professional (and dangerous) solvents.

Also, L-ascorbic acid is unstable, and this is what the main problem is.

Unstable L-ascorbic Acid

It is well known that L ascorbic acid is unstable.  It reacts with water and air, and will easily oxidize. Oxidized Vitamin C is not good for the skin, instead of an antioxidant, it becomes a pro-oxidant. This means that it will increase the formation of free radicals, instead of doing what it is supped to do and decrease free radicals in the skin.

Vitamin C derivatives

Many efforts have been made to use Vitamin C in skin care products. Most of these efforts have involved developing Vitamin C derivatives. For example, products such as: Ascorbyl palmitate, Magnesium ascorbyl phosphate, and Ascorbyl Tetraisopalmitate (also known as Tetrahexyldecyl Ascorbate).

Magnesium ascorbyl phosphate and Ascorbyl Tetraisopalmitate / Tetrahexyldecyl Ascorbate, have shown to increase collagen production, and they are good stable alternatives to L-ascorbic acid. However, it would be nice if we could still use the real deal.

Stable L-ascorbic acid in skin care products

Two other solutions have been developed. One is the L-ascorbic acid in silicone. I blogged about this recently, and you can read all about it here.

The other solution was offered by Pinnel and others in their paper “Ferulic Acid Stabilizes a Solution of Vitamins C and E and Doubles its Photoprotection of Skin”.

L-ascorbic acid with Ferulic acid

The Pinnell paper proposes that:

Ferulic acid is a potent ubiquitous plant antioxidant. Its incorporation into a topical solution of 15% L-ascorbic acid and 1% tocopherol improved chemical stability of the vitamins (C+E) and doubled photoprotection to solar-simulated irradiation of skin from 4-fold to approximately 8-fold as measured by both erythema and sunburn cell formation. Inhibition of apoptosis was associated with reduced induction of caspase-3 and caspase-7. This antioxidant formulation efficiently reduced thymine dimer formation. This combination of pure natural low molecular weight antioxidants provides meaningful synergistic protection against oxidative stress in skin and should be useful for protection against photoaging and skin cancer.

This study (and the patent) led to the Skinceuticals C E + Ferulic product. The Skinceuticals skin care product is certainly very popular and many people swear by it.

However, is it really stable?

This sentence “Ferulic acid is a potent ubiquitous plant antioxidant. Its incorporation into a topical solution of 15% L-ascorbic acid and 1% tocopherol improved chemical stability of the vitamins (C+E)” would suggest it is.

However, some forum members have commented that their product is colored orange, and an orange product with L-ascorbic acid means that the asacorbic acid has oxidized.

Did the Pinnell study also look at for how long Ferulic acid can stabilize a solution of Vitamin C and Vitamin E?

I don’t know, and it really does not matter, because this product is something that we can DIY ourselves.

The advantage of making your own version of Skinceuticals C+E+Ferulic is that it can be made fresh every week, so it will never oxidize.

In my next post I will discuss various DIY recipes for the SkinCeuticals product.  In the meantime there are already some recipes available on our website:  ce ferulic 1 and ce ferulic 2

Active ingredients for DIY Skinceuticals CE + Ferulic

http://www.bulkactives.com/ascorbicacid.htm

http://www.bulkactives.com/ferulicacidnatural.htm

http://www.bulkactives.com/dpanthenol.htm

http://www.bulkactives.com/nah.htm