PRODUCTS

PANTENOL

CAS Number: 16485-10-2
Preferred IUPAC name: 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Molecular Mass: 205.251,
EC Number: 240-540-6
Molecular Formula: C9H19NO4

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5.
In organisms, it is quickly oxidized to pantothenic acid.
Panthenol is a viscous transparent liquid at room temperature.
Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.

In pharmaceuticals, cosmetics, and personal-care products, panthenol is a moisturizer and humectant, used in ointments, lotions, shampoos, nasal sprays, eye drops, lozenges, and cleaning solutions for contact lenses.

In ointments it is used for the treatment of sunburns, mild burns, minor skin injuries, and disorders (in concentrations of up to 2–5%).
Panthenol improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing.
For this purpose, it is sometimes combined with allantoin.

Panthenol binds to the hair shaft readily, so, it is a common component of commercial shampoos and hair conditioners (in concentrations of 0.1–1%).
Panthenol coats the hair and seals its surface,[citation needed] lubricating the hair shaft and giving it a shiny appearance.

Panthenol is also recommended by tattoo artists as a post-tattooing moisturising cream.

Pharmacology
Panthenol readily penetrates into the skin and mucous membranes (including the intestinal mucosa), where it is quickly oxidized to pantothenic acid.
Pantothenic acid is extremely hygroscopic.
Panthenol is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and in cell growth.

Physical and chemical properties
Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders that are typically white. It is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100), in propylene glycol, and slightly soluble in glycerin.

Panthenol's expanded chemical formula is HO–CH2–C(CH3)2–CH(OH)–CONH–CH2CH2CH2–OH.

Stereochemistry
Panthenol comes in two enantiomers: D, and L. Only D-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in D form, or as a racemic mixture of D and L (DL-panthenol).

Chemical formula: C9H19NO4
Molar mass: 205.254 g·mol−1
Appearance: Highly viscous, colourless liquid
Density: 1.2 g mL−1 (at 20 °C)
Melting point: 66 to 69 °C (151 to 156 °F; 339 to 342 K) [contradictory]
Boiling point: 118 to 120 °C (244 to 248 °F; 391 to 393 K) at 2.7 Pa
log P: −0.989
Acidity: 13.033
Basicity: 0.964
Chiral rotation: +29° to +30°
Refractive index: 1.499
XLogP3-AA: -0.9
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 6
Exact Mass: 205.13140809
Monoisotopic Mass: 205.13140809
Topological Polar Surface Area: 89.8 Å²
Formal Charge: 0
Complexity: 182
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Widespread uses by professional workers
Panthenol is used in the following products: cosmetics and personal care products and perfumes and fragrances.
Other release to the environment of panthenol is likely to occur from: indoor use as processing aid.

Formulation or re-packing
Panthenol is used in the following products: cosmetics and personal care products.
Release to the environment of panthenol can occur from industrial use: formulation of mixtures.

If you looked around your home, you’d likely run across panthenol in several ingredients lists of products you own. Panthenol appears in food, supplements, and hygienic products of a wide variety.
Panthenol has a similar chemical structure to alcohol.
Panthenol is used to help hydrate and smooth your skin and hair from the inside in its ingestible form and from the outside in its topical form.

But is panthenol safe for you and your family when it appears in personal care products? Read on to find out why panthenol is in so many cosmetics and read the facts to understand how it affects your body.

Panthenol is a chemical substance made from pantothenic acid, also known as vitamin B-5. It occurs organically and can also be produced from both plant and animal sources. It’s used as an additive in various cosmetic products around the globe.

You very likely have pantothenic acid in your system right now, since it occurs in so many common food sources. And you’ve likely used a cosmetic or personal care product with panthenol within the last 24 hours.

Panthenol takes the form of either a white powder or a transparent oil at room temperature. You will sometimes see panthenol listed under one of its other names on ingredients list,
including:
dexpanthenol
D-pantothenyl alcohol
butanamide
alcohol analog of pantothenic acid
provitamin B-5

When absorbed into the body, panthenol becomes vitamin B-5.

Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium.
Panthenol exists as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol). While pantothenic acid is optically active, only the dextrorotatory form (Dexpanthenol) is biologically active.

Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium 1.

Due to its good penetration and high local concentrations, dexpanthanol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing.
Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing.
Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

Pharmacodynamics
Pantothenic acid is a precursor of coenzyme A, which serves as a cofactor for a variety of enzyme-catalyzed reactions involving transfer of acetyl groups.
The final step in the synthesis of acetylcholine consists of the choline acetylase transfer of acetyl group from acetylcoenzyme A to choline.
Acetylcholine is the neurohumoral transmitter in the parasympathetic system and as such maintains the normal functions of the intestine. Decrease in acetylcholine content would result in decreased peristalsis and in extreme cases adynamic ileus.

Mechanism of action
Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium.
Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium 1.

Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing.
Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

Panthenol, also known as provitamin B5, is the biologically active precursor of vitamin B5 (pantothenic acid).
A major physiological function of vitamin B5 is its conversion to acetyl coenzyme A (acetyl CoA), which participates in many metabolic processes involving carbohydrates, lipids, and proteins. Panthenol is essentially the alcohol form of vitamin B5.

Panthenol is most well known for its humectant properties—it is hygroscopic—thereby leading to its inclusion in moisturizing formulations.
Several reports in the literature highlight panthenol’s moisturizing properties and ability to improve the appearance and physical properties (e.g., smoothness) of skin.

In addition, topically applied panthenol helps to heal wounds, burns, and dermatitis.
There have been reports purporting the anti-inflammatory activity of panthenol, which would explain its efficacy as a healing agent.
In fact, a clinical study demonstrated the anti-inflammatory efficacy of nanotopes loaded with panthenol in the treatment of erythema induced by UV radiation.
Moreover, it was shown to alleviate inflammation caused by sodium lauryl sulfate treatment.
A recent study demonstrated that gene expression is modulated as a result of panthenol treatment during wound healing.10

Panthenol is also used in hair care compositions—mostly in conditioner and shampoo formulations—for its humectant properties.
A search of the patent literature reveals a number of inventions in which panthenol is used in combination with other ingredients as an adjuvant treatment in hair care.
However, there are no comprehensive reports in the scientific literature examining the benefits of panthenol in the treatment of hair.

The detection of the concentration of panthenol in cosmetic and pharmaceutical formulations is important from a quality control and product stability standpoint.
A number of studies have focused on chromatography technicques, alone or in combination with mass spectrometry.
Other methods take advantage of the optical properties of panthenol and employ colorimetric or spectrofluoremetric determination of the chromophore.

Panthenol is a multi-functional active ingredient that would be useful in most skin care formulations. Its efficacy has been substantiated in numerous peer-reviewed journals.
The biologically active form of Panthenol, D-panthenol (EU), is the stable alcohol analogue of vitamin B5, pantothenic acid (EU), and is quickly converted to vitamin B5 (pantothenate) in the body.
Pantothenic acid is present in all living cells and acts as an essential nutritional component due to its role in the formation of acetyl-co-enzyme A in the early stages of metabolism.

The main role of acetyl-co-enzyme A is to provide activated acetic acid into the citric acid cycle (Krebs Cycle).
This produces carbon dioxide, water, and energy. Co-enzyme A also transfers to other molecules such as Nacetyl-glucosamine (EU) and acetylcholine (EU) to help in the production of steroids and the synthesis of fatty acids.
Coenzyme A also helps the body detoxify foreign substances.

During synthetic preparation of panthenol, the racemic mixture (DL-panthenol, containing 50:50 of each form) is formed.
Biological activity occurs only for D-Panthenol (Dex-Panthenol); literature methods for synthesis of only D-panthenol exist.
For cosmetic use, Panthenol can be obtained in the D form, or as the racemic mixture. D-Panthenol is a highly viscous transparent liquid at room temperature.
However, DL-Panthenol and salts of pantothenic acid are white powders.
Both forms are soluble in water, alcohol, propylene glycol (EU), ether (EU), chloroform (EU), and slightly soluble in glycerin (EU).

Benefits of Panthenol
Repairs and strengthens damaged hair, thickens hair, reduces split ends and increases the tensile strength of the hair
Stimulates wound healing. Synergy with zinc oxide is claimed.
Enhances skin barrier repair and reduces inflammation after sodium lauryl sulphate-induced irritation.
Anti-inflammatory activity. Can increase sun-protection factor (SPF).
Panthenol stimulates the proliferation of dermal fibroblasts and can accelerate cell turnover.
Has anti-aging benefits. Synergism with niacinamide (Vitamin B-3) is claimed.
It’s a penetrating moisturizer. Can penetrate and hydrate nails and hair.
Protects lips against solar-induced herpes.

Pantothenic acid exists in all living cells and tissues.
Panthenol is a component of coenzyme A, and it is involved in releasing energy from carbohydrates, as well as helping the body use fats and proteins, among other things.
Panthenol dissolves in water.
The conventional manufacturing process of panthenol involves chemical condensation of synthetic R-pantolactone (α-hydroxy-β,β-dimethyl-γ-butyrolactone) with 3-aminopropanol.

The alcohol analog of pantothenic acid, and is thus a provitamin of B₅.
In organisms it is quickly oxidized to pantothenic acid.
Panthenol is a viscous transparent liquid at room temperature.
Used as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.

An easy-to-formulate, commonly used, nice to have ingredient that’s also called pro-vitamin B5.
As you might guess from the “pro” part, it’s a precursor to vitamin B5 (whose fancy name is pantothenic acid).

Its main job in skincare products is to moisturise the skin.
It’s a humectant meaning that it can help the skin to attract water and then hold onto it.
There is also research showing that panthenol can help our skin to produce more lovely lipids that are important for a strong and healthy skin barrier.

Another great thing about panthenol is that it has anti-inflammatory and skin protecting abilities.
A study shows that it can reduce the irritation caused by less-nice other ingredients (e.g. fragrance, preservatives or chemical sunscreens) in the product.

Research also shows that it might be useful for wound healing as it promotes fibroblast (nice type of cells in our skin that produce skin-firming collagen) proliferation.

If that wasn’t enough panthenol is also useful in nail and hair care products.
A study shows that a nail treatment liquide with 2% panthenol could effectively get into the nail and significantly increase the hydration of it.

As for the hair the hydration effect is also true there.
Panthenol might make your hair softer, more elastic and helps to comb your hair more easily.

Panthenol is well absorbed into the skin and quickly converted into Pantothenic acid by oxidation. Pantothenic acid is distributed into the cells and is converted to Acetyl Coenzyme-A (Acetyl CoA) in the cells of the epidermis.
Human being require Vitamin B5 to synthesize Acetyl CoA which is an essential mediator to many biochemical reactions that sustain life (maintenance and repair of all cells) and which breaks down fats, carbohydrates and proteins for carbon dioxide, water, and energy generation.
Furthermore, it synthesis fatty acids and sphingolipids, for stratum corneum lipid layers and cell membrane integrity & fluidity.

Synomys:
DL-Panthenol
panthenol
16485-10-2
DL-Pantothenol
DL-Pantothenyl alcohol
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Panthenolum
Pantenol
Pantenolo
(+-)-Pantothenyl alcohol
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-
Alcool DL-pantotenilico
Panthenol, racemic
MFCD00002944
Penthenol
Varitan
D-(+)-Panthenol
Provitamin B5
D-(+)-Pantothenyl alcohol
Dexpantenol
Dexpanthenolum
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
DL-Pantothenol;DL-Pantothenyl alcohol
Panthenol , DL-form
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (+)- (9CI)
62507-76-0
Pantenolo [DCIT]
Pantenol [INN-Spanish]
Panthenolum [INN-Latin]
component of Zentinic
Panthenol, (+)-
SMR000857333
N-Pantoyl-3-propanolamine
Alcool DL-pantotenilico [Italian]
SR-05000001760
EINECS 240-540-6
NSC302962
d,l- panthenol
Fancol DL
NCGC00186658-01
pantothenylol alcohol
ACMC-20ajzi
Dexpanthenol [USAN)
DL-Panthenol 99%
Panthenol [USAN:USP:INN:BAN:JAN]
2,3-dimethylbutyramide
DL-Panthenol, 99%
ACMC-209pkr
Panthenol (USP/INN)
(+-)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
ACMC-1AYN9
compnent of ilopan-Choline
EC 240-540-6
DSSTox_CID_24598
DSSTox_RID_80341
DSSTox_GSID_44598
SCHEMBL15567
MLS001336015
MLS001336016
(R)-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
CHEMBL1371937
D-(+)-2,3-dimethylbutyramide
DTXSID3044598
HMS2093B14
HMS2234M16
HMS3371M11
Pharmakon1600-01505420
Pharmakon1600-01505656
HY-B1024
Tox21_302660
ANW-22120
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (+-)-
Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, DL-
NSC759127
NSC759899
s4566
STL453540
AKOS015841508
CCG-213502
CS-4541
EBD2293971
MCULE-2403906933
NSC 759899
NSC-302962
NSC-759127
NSC-759899
VC31151
NCGC00256864-01
AK-60852
AK113720
AS-56363
DA-09547
P992
SBI-0206818.P001
CAS-16485-10-2
DB-056494
FT-0625499
FT-0625596
FT-0693817
P1318
A19436
D03726
AB00918367_05
A810597
Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3
Q196473
Q-201031
SR-05000001760-1
SR-05000001760-3
3-(2,4-Dihydroxy-3,3-dimethylbutyramido)-1-propanol
BRD-A59413292-001-04-1
Butanamide,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-
3,3-dimethyl-2,4-bis(oxidanyl)-N-(3-oxidanylpropyl)butanamide
D-2,4-Dihydroxy-3,3-dimethyl-N-(3-hydroxypropyl)butyramide
Butanamide,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)-
Butyramide,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)-
Panthenol, racemic, United States Pharmacopeia (USP) Reference Standard