PANTHENOL

Synonyms:
DL-Panthenol; panthenol; 16485-10-2; DL-Pantothenol; DL-Pantothenyl alcohol; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide; Panthenolum; Pantenol; Pantenolo; Pantenolo [DCIT]; Urupan; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-; Alcool DL-pantotenilico; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)- ; Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)- ;Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (2R)- ; D Panthenol; DPanthenol; d panthenol; dpanthenol; D PANTHENOL; D-Panthenol; d pantenol; D PANTENOL; d pantenol; DPANTENOL; dpantenol; DEXPANTHENOL; dexpanthenol; dexpantenol; DEXPANTENOL;Dexpanthenol; DEKSPANTHENOL; DEKSPANTENOL; dekspanthenol; dekspantenol; dexpanthenolum; DEXPANTHENOLUM; dekspanthenolum; DEKSPANTHENOLUM;Dexpanthenolum; PROPONOLAMINE; PROPONOLAMİNE; proponolamın; proponolamin; d-Pantothenyl alcohol; Bepanthen; Propanolamine, N-pantoyl-; n pantoyl; n pantoyil; alkol; bepanten; BEPANTEN; D-Panthenol; D-Panthoenyl alcohol; Provitamin B5.; D-PANTHENOL; DL-Panthenol; 16485-10-2; panthenol; DL; Pantothenol; DL-Pantothenyl alcohol; Panthenolum; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide; Pantenol; Pantenolo; Penthenol; Varitan; (+-)-Pantothenyl alcohol; Pantenolo [DCIT]; Urupan; Panthenol , DL-form; Alcool DL-pantotenilico; Pantenol [INN-Spanish]; Panthenolum [INN-Latin]; Pantothenylol; Intrapan; Pantenyl; D-(+)-Panthenol; C9H19NO4; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-; Provitamin B5; Alcool DL-pantotenilico [Italian]; Dextro pantothenyl alcohol; EINECS 240-540-6; Alcopan-250; D-(+)-Pantothenyl alcohol; Dexpantenol; Dexpanthenolum; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide; Pantothenol, D-; Dexpantenol [INN-Spanish]; Dexpanthenolum [INN-Latin]; EINECS 201-327-3; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (+-)-; Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, DL- component of Zentinic; Panthenol, (+)-;D-PANTHENOL; DL-Panthenol; 16485-10-2; panthenol; DL; Pantothenol; DL-Pantothenyl alcohol; Panthenolum; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide; Pantenol; Pantenolo; Penthenol; Varitan; (+-)-Pantothenyl alcohol; Pantenolo [DCIT]; Urupan; Panthenol , DL-form; Alcool DL-pantotenilico; Pantenol [INN-Spanish]; Panthenolum [INN-Latin]; Pantothenylol; Intrapan; Pantenyl; D-(+)-Panthenol; C9H19NO4; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-; Provitamin B5; Alcool DL-pantotenilico [Italian]; Dextro pantothenyl alcohol; EINECS 240-540-6; Alcopan-250; D-(+)-Pantothenyl alcohol; Dexpantenol; Dexpanthenolum; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide; Pantothenol, D-; Dexpantenol [INN-Spanish]; Dexpanthenolum [INN-Latin]; EINECS 201-327-3; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (+-)-; Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, DL-component of Zentinic; Panthenol, (+)-; pantenol; panthenol; panthenole; pantenol; pantenole; panthenol; panthenol; pantenol; Panthenole ;pantenol

PANTHENOL

Panthenol

Panthenol
Stereo, skeletal formula of panthenol (R)
Names
IUPAC name
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide[1]
Other names
Pantothenol
Pantothenyl alcohol
N-Pantoylpropanolamine
Bepanthen (trade name)
Dexpanthenol (D form)
Identifiers
CAS Number    
16485-10-2 ☒
81-13-0 R ☒
3D model (JSmol)    
Interactive image
3DMet    
B00882
Beilstein Reference    1724945, 1724947 R
ChEBI    
CHEBI:27373 ☒
ChEMBL    
ChEMBL1200979 ☒
ChemSpider    
4516 check
115991 R ☒
4677984 S ☒
ECHA InfoCard    100.036.839
EC Number    
240-540-6
KEGG    
D03726 check
MeSH    dexpanthenol
PubChem CID    
4678
131204 R
5748487 S
RTECS number    
ES4316500
UNII    
1O6C93RI7Z check
CompTox Dashboard (EPA)    
DTXSID3044598
InChI[show]
SMILES[show]
Properties
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 (pKa)    13.033
Basicity (pKb)    0.964
Chiral rotation ([α]D)    +29° to +30°
Refractive index (nD)    1.499
Pharmacology
ATC code    A11HA30 (WHO) D03AX03 (WHO), S01XA12 (WHO)
Hazards
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
110
Lethal dose or concentration (LD, LC):
LD50 (median dose)    10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
Related compounds
Related compounds    
Arginine
Theanine
Pantothenic acid
Hopantenic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
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. It is a viscous transparent liquid at room temperature. Panthenol is used as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.

Uses

Bepanthen eye and nose ointment (Germany)
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%).[2] It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing.[3] For this purpose, it is sometimes combined with allantoin.

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

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

Adverse effects
Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported.[2][3]

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,[4] that is, it binds water effectively. It is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and thus in cell growth.[2][3]

Physical and chemical properties

Dexpanthenol
Panthenol is an odourless, slightly bitter, highly viscous, transparent and colourless liquid at room temperature,[5] but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100),[5] 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).

D-Panthenol
D-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. D-Pantenol is a viscous transparent liquid at room temperature. D-Panthenol is used as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.

Bepanthen eye and nose ointment (Germany)
In pharmaceuticals, cosmetics and personal-care products, D-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%).[2] It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing.[3] For this purpose, it is sometimes combined with allantoin.

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

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

Adverse effects
D-Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported.[2][3]

Pharmacology
D-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,[4] that is, it binds water effectively. It is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and thus in cell growth.[2][3]

Physical and chemical properties

Dexpanthenol
D-Panthenol is an odourless, slightly bitter, highly viscous, transparent and colourless liquid at room temperature,[5] but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). D-Pantenol is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100),[5] in propylene glycol, and slightly soluble in glycerin.

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

Stereochemistry
D-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).

In cosmetics, panthenol is a humectant, emollient and moisturizer. D-Panthenol binds to hair follicles readily and is a frequent component of shampoos and hair conditioners (in concentrations of 0. 1-1%). D-Panthenol coats the hair and seals its surface, lubricating follicles and making strands appear shiny. Panthenol is the alcohol analog of pantothenic acid (vitamin B5), and is thus the provitamin of B5. In organisms it is quickly oxidized to pantothenate. Panthenol is a viscous transparent liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). D-Panthenol is well soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin.

Overview
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. D-Panthenol has a similar chemical structure to alcohol. D-Panthenol’s 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 D-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.

What is d-panthenol?
d-Panthenol is a chemical substance made from pantothenic acid, also known as vitamin B-5. D-Panthenol occurs organically and can also be produced from both plant and animal sources. D-Panthenol’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 D-Panthenol within the last 24 hours.

D-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.

What’s D-Panthenol used for?
In topical cosmetics, product manufacturers often use panthenol as a moisturizer. But D-Panthenol’s also included in many cosmetics as a softening, soothing, and anti-irritant agent.D-Panthenol also helps your skin build up a barrier against irritation and water loss.

Skin products
Vitamin B-5 is essential for a healthy diet, skin, and hair. D-Panthenol makes sense that panthenol, its derivative, is a staple of many skin care products, such as lotions and cleansers. D-Panthenol’s also found in cosmetics as various as lipstick, foundation, or even mascara.D-Panthenol also appears in creams made to treat insect bites, poison ivy, and even diaper rash.

The National Center for Biotechnology Information lists panthenol as a skin protectant with anti-inflammatory properties. D-Panthenol can help improve skin’s hydration, elasticity, and smooth appearance. D-Panthenol also soothes:

red skin
inflammation
little cuts or sores like bug bites or shaving irritation
D-Panthenol helps with wound healing, as well as other skin irritations like eczema.

Hair products
Hair care products include D-Panthenol because of its ability to improve your hair’s:

shine
softness
strength
D-Panthenol can also help protect your hair from styling or environmental damage by locking in moisture.

One study found that panthenol may help slow down and hide the look of thinning hair. The study tested it with other active ingredients as a leave-in treatment.

Nail products
Your nails are made from keratin proteins, just like your hair. So, D-Panthenol follows that panthenol can strengthen your finger- and toenails. You might find it in your shine and strengthening nail treatments, or in hand creams and cuticle oils.

One study found that applying panthenol to the nail can help hydrate the nail and prevent breakage.

Molecular Weight of Panthenol:     205.25 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3-AA of Panthenol:    -0.9    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Panthenol:    4    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Panthenol:    4    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Panthenol:    6    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Panthenol:    205.131408 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Panthenol:    205.131408 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Panthenol:    89.8 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Panthenol:    14    Computed by PubChem
Formal Charge of Panthenol:    0    Computed by PubChem
Complexity of Panthenol:    182    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Panthenol:    0    Computed by PubChem
Defined Atom Stereocenter Count of Panthenol:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Panthenol:    1    Computed by PubChem
Defined Bond Stereocenter Count of Panthenol:    0    Computed by PubChem
Undefined Bond Stereocenter Count of Panthenol:    0    Computed by PubChem
Covalently-Bonded Unit Count of Panthenol:    1    Computed by PubChem
Compound  of Panthenol Is Canonicalized    Yes