Tyrostan - Sinerga

the
Sun
all year
long
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the
Sun
all year
long
summary
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TYROSTAN®
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skin pigmentation
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tyrosine and its derivatives in cosmetic products
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applications
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pigmentation efficacy following UV irradiation
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formulations
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bibliography
TYROSINE
soluble at pH insoluble in water
• key substance
in melanogenesis
CAPROIC ACID
(as the potassium salt)
• mild antioxidant
POTASSIUM
CAPROYL TYROSINE
an easytouse Nacyl derivative
of tyrosine is obtained via
the condensation of tyrosine with
caproic acid (as the potassium salt)
delivering the equivalent
of about pure tyrosine
TYROSTAN
completely clear liquid;
water soluble;
compatible with traditional
cosmetic ingredients
• tanning magnifier
• increases the amount of
available tyrosine
Cosmetic applications as a tanning magnifier of POTASSIUM
CAPROYL TYROSINE have been developed in suncare products before
exposure during exposure and for suntan maintenance after exposure
The stability of POTASSIUM CAPROYL TYROSINE over time has been
confirmed in several formulations including cleansers gels and
emulsions
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SKIN PIGMENTATION
Melanogenesis occurs as a protective defense of the skin to UVB rays but includes
the initial pigmentation activated by UVA rays as part of a series of chain reac
tions which generate the final and permanent pigmentation ()
The pigmentation of human skin can be the result of two different mechanisms:
) Melanin biosynthesis at the melanocytes
) a simple reaction between skin proteins and specific reactive substances in the
horny layer
Additionally there are other types of products that produce an "artificial" tan without sun
light: bronzers extenders tanning pills and tanning magnifiers (
)
In particular TANNING MAGNIFIER
are substances that when
applied to the skin will increase
melanin production in sunlight
by increasing the substrate avai
lable for tyrosinase activity the
key enzyme in melanogenesis The tanning process is therefore
hastened by stimulating the pro
duction of melanin by ingre
dients such as tyrosine or tyrosi ne derivatives
The use of tyrosine is based upon
the presumption that it penetra
tes the skin increases the tyrosi
ne content of the melanocytes
and thus enhances melanin for
mation ()
Melanogenesis could become a
more continous process with a
constant concentration of tyrosi
ne without affecting the rate of
production of melanin
The melanin expressed from melanocytes can be further defined as: eumelanins
feomelanins and tricochromes () These three different types of pigments are
derived from a common parent compound LTyrosine a nonessential amino acid
synthesized in the body from phenylalanine
LTyrosine also has other physiological functions: it is a precursor of the neuro
transmitters such as norepinephrine and dopamine both of which regulate mood
adrenalin (adrenocortical hormone) and thyroxine (thyroid hormone)
Tyrosine deficiency has been linked to:
• HYPOTHYROIDISM
• LOW BLOOD PRESSURE
• LOW BODY TEMPERATURE
• RESTLESS LEG SYNDROME
LTyrosine is related to the pigment for hair and skin color because is the starting
material for melanin biosynthesis In this regard not only is the concentration of
tyrosine important (effecting the activity of tyrosinase the catalytic enzyme in
melanogenesis) but also its bioavailability()
Because tyrosine binds unstable molecules that can potentially cause damage to
the cells and tissues it can be considered as a mild antioxidant
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TYROSINE AND ITS DERIVATIVES IN COSMETIC PRODUCTS
All these considerations lead to the development of cosmetic skin products containing
tyrosine for the purposes of increasing (or magnifying) and maintaining skin tanning
Thus attempts to enhance melanogenesis by altering LTyrosine availability are
based on the concept that the concentration of the primary substrate for tyrosina
se (tyrosine) may be a limiting factor ()
But different experiences have shown that pure tyrosine as a topical application
does not have acceptable bioavailability
In fact pure tyrosine is only soluble at pH a value at which keratin destruc
tion occurs At lower pH tyrosine crystallizes and therefore cannot be absorbed
Tyrosine has poor solubility in water (
g/dl at RT)
Other experiments show that the minimum concentration of Ltyrosine in the
applied product must be greater than • POTASSIUM CAPROYL TYROSINE (*)
An easytouse Nacyl derivative of tyrosine has been obtai
ned via the condensation of tyrosine with capryc acid (as the
potassium salt) delivering the equivalent of about pure
tyrosine ()
It is a clear liquid completely water soluble and compatible
with traditional cosmetic ingredients similar to other lipo
amino acids oligopeptides and watersoluble amino acids
*(supplied by Sinerga under the trade name TYROSTAN)
• CAPROYL TYROSINIC ACID SORBITAN ISOSTEARATE GLYCERYL OLEATE
(supplied by SINERGA under the trade name TYROSINOL)
is the corresponding lipophilic form and its properties are:
PROPERTIES OF TYROSINOL
APPEARANCE
Clear liquid
COLOR
Light Yellow
ODOR
Characteristic
pH (c)
n a
SOLUBILITY
Complete in lipophilic systems
CAPROYL TYROSINIC ACID ()
DRY RESIDUE
TYROSINOL Caproyl Tyrosinic acid Sorbitan Isostearate Glyceryl Oleate is a lipo
philic functional product compatible with traditional cosmetic ingredients and the
refore particularly indicated for all “SUN PRODUCTS” formulations such as Oils
Lipogels Anhydrous Sticks etc
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APPLICATIONS
BEFORE
Sun Exposure
• prepares the skin
by increasing
melanogenesis
AFTER
Sun Exposure
• mild antioxidant
• skin tan
maintenance
• healthy face tone
DURING
Sun Exposure
• through melanogenesis
the skin is protected
from UV rays
BABY SUN SPRAY WATER
(SPRAY SOLUTION)
SUN TAN GEL (ACTIVATOR SUN GEL)
SUN TAN OIL (ACTIVATOR SUN OIL)
DAY CREAM
(LIGHT EMULSION)
BATHSHOWER
AFTER SUN BODY LOTION
(O/W FLUID EMULSION)
SUGGESTED DOSAGE PROPERTIES OF TYROSTAN
Chemical name
POTASSIUM CAPROYL TYROSINE
INCI name (EU)
POTASSIUM CAPROYL TYROSINE
INCI name (USA) POTASSIUM CAPROYL TYROSINE
– Appearance
Clear liquid
pH ( sol)
Color
From yellow to amber yellow
Activity
Odor
Slight characteristic
Solubility
Complete in water
TOXICOLOGICAL PROFILE
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Dry residue (
°C )
Skin irritation
Non irritating
Eye irritation
Non irritating
Skin Sensitisation
Non sensitising
TOLERABILITY
The toxicological profile has been performed by in vitro
testing according to the Irritation Assay System protocol
with the aim of defining the occurence of potential der
mal irritation This test is a reliable substitute for the
patch test normally used Results of the study indicated
that the sample is classified as a non irritating agent
PIGMENTATION EFFICACY FOLLOWING UV IRRADIATION
The cosmetic efficacy of the product has been evaluated in comparison with a pla
cebo and an untreated control area
PCT was formulated at a concentration in a emulsiongel applied on the back
of volunteers phototypes II III IV (according to Fitzpatrick definition) for
three consecutive weeks using a solar simulator (Multipolar solar UV)
The effect on the skin was evaluated with Chromameter (CR Minolta) up to weeks after the application ( )
Steps of the procedure during weeks were the following:
• T basal colorimetric measurements (day )
• T st colorimetric measurements (day )
• T nd colorimetric measurements (day )
• T rd colorimetric measurements (day )
• T th colorimetric measurements (day )
Final measurements were done at T and the removal of non occlusive patches
and application of the product sample and placebo was done at any time
The exposure to UVAUVB rays was done at MEDu
The pigmentation efficacy is shown by a decrease in ITA° values (Individual
Typological Angle) that expresses the melanin index calculated from L* and b*
parameters
TABLE SHOWS ITA° MEAN VALUE CALCULATED FOR EACH AREA AT EACH MEASUREMENT
POTASSIUM
CAPROYL
TYROSINE
CONTROL AREA
PLACEBO
RESULTS
The area treated for weeks with POTASSIUM CAPROYL TYROSINE at showed
a highly significant decrease in ITA° after exposure to UVAUVB radiation at T to
T This decrease was indicative of increased pigmentation; the area treated with
placebo did not show a significant decrease in ITA° nor did the untreated control
area at any time(
) Regarding data on efficacy evaluations: variance analysis and
Tukey test were carried out in order to determine statistically significant differen
ces among the set of values recorded at different times in the three areas:
• the area treated with the sample of PCT at showed a highly significant
decrease in ITA° values (T versus T p and T versus T p )
• the area treated with the sample of Placebo did not show a significant decrease
in ITA° values at any time
• the control area untreated did not show a significant decrease in ITA° values at
any time
The graph shows the ITA° values recorded It can be noted that the values recorded in
the control area treated with the two products are often lower than those recorded in
the control area That means a tendency to a pigmentation increase The difference of
values is nevertheless not significant (p
) The test product is significantly effec
tive in increasing the skin tanning in comparison to the start conditions A similar level
of significance could not be obtained in the comparison with the reference areas pro
bably because of the high standard deviation
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BABY SUN SPRAY WATER
INCI NAME
• WATER
qb
AQUA
• GRAMBEN II
Sinerga
PROPYLENE GLYCOL
DIAZOLIDINYL UREA
METHYLPARABEN
PROPYLPARABEN
• FRAGRANCE
PARFUM
• RESASSOL VH
PGGBUTETH
PEG HYDROGENATED
CASTOR OIL
• TYROSTAN
Cosmetic formulations containing
of Potassium Caproyl Tyrosine
have been developed
considering areas of potential
application (
)
Sinerga
POTASSIUM CAPROYL
TYROSINE
• EDTA
DISODIUM EDTA
Typical properties:
pH:
FORMULATIONS
DAY CREAM
INCI NAME
• PHYTOCREAM Sinerga
POTASSIUM PALMITOYL
HYDROLYZED WHEAT PROTEIN
GLYCERYL STEARATE
CETEARYL ALCOHOL
• DRAGOXAT EH
ETHYLHEXYL
ETHYLHEXANOATE
• SF Sinerga
DIMETHICONE
• WATER
qb
SUN TAN GEL
INCI NAME
• WATER
AQUA
• FENOSSIPARABEN
Sinerga
• PEMULEN TR • CARBOPOL ULTREZ Sinerga
Sinerga
CARBOMER
• DRAGOXAT EH
OCTYL OCTANOATE
• SEAMOLLIENT
• FINSOLV TN
AQUA ALGAE
C
ALKYL BENZOATE
• PHYTOPROLIN COMPLEX
Sinerga
HYDROLYZED VEGETABLE PROTEIN
• TYROSTAN
Sinerga
POTASSIUM CAPROYL
TYROSINE
• AMP SODIUM CARBOMER
• FRAGRANCE
ACRYLATES / C
ALKYL ACRYLATE CROSSPOLYMER
POTASSIUM CAPROYL
TYROSINE
• PNC IMIDAZOLIDINYL UREA
SQUALENE
• TYROSTAN
qb
AQUA
• GRAM PHENOXYETHANOL
METHYLPARABEN
BUTYLPARABEN
PROPYLPARABEN
• PHYTOSQUALANE
AMINOMETHYL PROPANOL
PARFUM
Typical properties:
pH:
Viscosity at °C:
9
mPas
Typical properties:
pH:
Viscosity at °C:
mPas
SUN TAN OIL
AFTER SUN BODY LOTION
INCI NAME
INCI NAME
• SF
Sinerga
DIISOPROPYL ADIPATE
• FINSOLV TN
• DRAGOXAT EH
C ALKYL BENZOATE
• DRAGOXAT EH
Sinerga
ETHYLHEXYL ETHYLHEXANOATE
• FINSOLV TN
ETHYLHEXYL ETHYLHEXANOATE
• PARSOL MCX
POTASSIUM PALMITOYL
HYDROLYZED WHEAT PROTEIN
GLYCERYL STEARATE
CETEARYL ALCOHOL
CYCLOPENTASILOXANE
• CERAPHYL • PHYTOCREAM C
ALKYL BENZOATE
• SF /
ETHYLHEXYL
METHOXYCINNAMATE
Sinerga
DIMETHICONE
• FRAGRANCE
• APEROXID TLA
PARFUM
• TYROSINOL
Sinerga
CAPROYL TYROSINIC ACID
SORBITAN ISOSTEARATE
GLYCERYL OLEATE
TOCOPHEROL
LECITHIN ASCORBYL PALMITATE
CITRIC ACID
• FENOSSIPARABEN
Sinerga
PHENOXYETHANOL
METHYLPARABEN
BUTYLPARABEN
PROPYLPARABEN
• WATER
qb
AQUA
• GRAM Sinerga
IMIDAZOLIDINYL UREA
• EDTA Na
DISODIUM EDTA
• KELTROL
XANTHAN GUM
• MANDORLAT
Sinerga
PRUNUS AMYGDALUS DULCIS
HYDROLYZED SWEET ALMOND PROTEIN
POTASSIUM PALMITOYL HYDROLYZED
WHEAT PROTEIN
• GLYCERIN
GLYCERIN
• SEAMOLLIENT
AQUA ALGAE
• TYROSTAN
BATHSHOWER DETERGENT
Sinerga
POTASSIUM CAPROYL
TYROSINE
INCI NAME
• FRAGRANCE
• TRITON CG
Sinerga
CAPRYLYL/CAPRYL GLUCOSIDE
• ZETESOL LES SODIUM LAURETH SULFATE
• LAUROAT
PARFUM
Sinerga
Sinerga
Typical properties:
pH
Viscosity at °C:
mPas
SODIUM LAUROYL OAT AMINOACIDS
• AVENOLAT
AVENA SATIVA HYDROLYZED
OAT PROTEIN POTASSIUM PALMITOYL
HYDROLYZED OAT PROTEIN
• AVENOPEPTIDE
Sinerga
• COCOYL WHEAT AMINOACIDS Sinerga
HYDROLYZED OAT PROTEIN
SODIUM COCOYL WHEAT
AMINOACIDS
• WATER
qb
AQUA
• GRAM Sinerga
Sinerga
IMIDAZOLIDINYL UREA
• FENOSSIPARABEN
PHENOXYETHANOL
METHYLPARABEN
BUTYLPARABEN
PROPYLPARABEN
• SODIUM CHLORIDE
SODIUM CHLORIDE
• ANTIL PEG METHYL
GLUCOSE DIOLEATE
• TYROSTAN
POTASSIUM CAPROYL
TYROSINE
• LAUROAMIDOPROPYL BETAINE
• CITRIC ACID
• FRAGRANCE
Sinerga
Conclusions
POTASSIUM CAPROYL TYROSINE is
water soluble and CAPROYL TYROSI
NIC ACID SORBITAN ISOSTEARATE
GLYCERIN OLEATE is soluble in oil
and both are clear and easy to add to
cosmetic formulations where a tan
magnifying effect is requested with
significant efficacy modulated in
time In formulating the advice is to
add the tanning magnifier after the
emulsifying phase at about °C or at
any time during cooling phase
To insure its stability it is suggested to
avoid its contact with strong oxidizing
agents and alkaline solutions
Recommended use level is PARFUM
Typical properties:
pH:
Viscosity at °C:
mPas
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BIBLIOGRAPHY
Brown DA J Photochem Photobiol B () ()
US Food and Drug Administration Federal Register () ()
N Muzzuidin et al Skin Res and Technol () ()
AA Chem Eng News () ()
Levy SB Dermatol Clin () ()
Prota G Cosm Toil Ed It ()
Camacho et al Arch Dermatol ()
Slominski et al Pigment Cell Res ()
P P Agin et al Photochem Photobiol ()
W Tur Cosm Toil ()
C Jaworsky et al J Am Acad Dermatol ()
H Sedghi Zadeh Cosm News ()
G H Pittel Drug Cosm Ind ()
Lowe N J et al Clin Dermatol () ()
G Guglielmini Cosm Technol () ()
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SINERGA SpA
Headquarters and Research Centre:
Via Pitagora Pero
Milan (Italy)
Tel Fax Factory:
Via della Pacciarna Gorla Maggiore
Varese (Italy)
Tel Fax Email: vendite@sinergait
Web site: wwwsinergait
SINERGA FRANCE Sarl
Lieu dit la Montjoie Rue de la Procession
La Plaine Saint Denis
Tel Fax Email: sinerga@wanadoofr
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