DEXPANTHENOL

Dexpanthenol is an alcohol analog of pantothenic acid and an important component of parenterals, local cosmetic preparations and multi-vitamins. 
Dexpanthenol has as much biological activity as pantothenic acid and is found to be stable in aqueous solution.

CAS:    81-13-0
MF:    C9H19NO4
MW:    205.25
EINECS:    201-327-3

Dexpanthenol belongs to a derivative of pantothenic acid (vitamin B5). 
Dexpanthenol can penetrate the skin and mucous membrane to be quickly oxidized to pantothenic acid. 
The later one is extremely hygroscopic and binds water effectively. 
Therefore, Dexpanthenol can be used as a moisturizer. 
Dexpanthenol is added to pharmaceutical and cosmetic products to relieve itching and improve wound healing. 
In ointments, Dexpanthenol can be used for the treatment of sunburns, mild burns, minor skin injuries and disorders. 

Dexpanthenol is also immediately applied after major abdominal surgery to minimize the possibility of paralytic ileus. 
In addition, Dexpanthenol can also be supplemented into the commercial shampoos and hair conditioners to lubricate the hair shaft and give the hair a shiny appearance. 
The exact mechanism of action of Dexpanthenol is still unclear, perhaps through its enhancing effect on acetylcholine.  

A moisturiser and humectant (which means it soaks up water and retains it) - Dexpanthenol calms and repairs dry, cracked, irritated skin. 
Often found in creams, ointments and other topical products, dexpanthenol can be a hydrating lifeline to those who are plagued by dry, tight skin. 

Dexpanthenol’s powers don’t stop at healing and hydrating, dexpanthenol can strengthen your skin’s natural barrier, making it less susceptible to dryness and its associated problems. 
Below we explore what is dexpanthenol and take a closer look at dexpanthenol cream and its uses.

Dexpanthenol is a derivative of pantothenic acid, a B complex vitamin. 
Dexpanthenol is usually applied topically in cream or lotion form to improve hydration and reduce water loss while helping to keep the skin soft and supple.
Dexpanthenol has good penetration qualities which means it is capable of sinking into the skin, enabling it to get to the heart of the problem rather than simply sitting on the skin’s surface. 

As well as being a moisturiser and skin protector, Dexpanthenol also has anti-inflammatory properties which makes it a perfect balm for calming raw, irritated skin.
Dexpanthenol is an alcoholic analogue of D-pantothenic acid that is used as a supplement or application to support a healthy epithelium and is also used to prevent vitamin deficiency in patients receiving total parenteral nutrition (TPN).

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

Due to Dexpanthenol's 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, Dexpanthenol acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

Dexpanthenol is also available as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol) as Panthenol. 
While pantothenic acid is optically active, only the dextrorotatory form (dexpanthenol) is biologically active.

Dexpanthenol is soluble in water and alcohol, although insoluble in fats and oil based substances. 
With the appropriate vehicle, Dexpanthenol is easily penetrated into the skin. 
Rate of penetration and absorption is reduced when Dexpanthenol is administered as an oil/water formula.

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

An alcoholic analogue of D-pantothenic acid and cholinergic agent. 
Dexpanthenol acts as a precursor of coenzyme A necessary for acetylation reactions and is involved in the synthesis of acetylcholine. 
Although the exact mechanism of the actions of dexpanthenol is unclear, it may enhance the effect of acetylcholine. 
Dexpanthenol acts on the gastrointestinal tract and increases lower intestinal motility. 
Dexpanthenol is also applied topically to the skin to relieve itching and to promote healing.

Dexpanthenol is an alcohol form of the B5 vitamin pantothenic acid. 
Dexpanthenol easily penetrates the skin retaining water and is a humectant, emollient and moisturizer. 
Dexpanthenol mitigates signs of inflammation and stimulates epithelization. 
Dexpanthenol comes in two enantiomers, D and L. 
Only Dexpanthenol is biologically active, however both forms have moisturizing properties. 

Because of the ability to attract and hold moisture panthenol is used in skincare products as a humectant. 
Dexpanthenol also has a role as provitamin (called pro-vitamin B5) and is used as a vitamin supplement in complex ( M.V.I. ADULT injection, Hospira Worldwide, Inc.) and alone, and as a cholinergic drug. 
Dexpanthenol is a highly viscous transparent liquid at room temperature, but salts of pantothenic acid (sodium pantothenate) are powders (typically white). 
Dexpanthenol is soluble in water, alcohol, propylene glycol, ether and chloroform, and slightly soluble in glycerin. 

Dexpanthenol mixes readily with many different types of ingredients, making it a versatile ingredient to be used in formulas because Dexpanthenol improves skin’s barrier function and maintains the proliferation of fibroblasts. 
In organisms Dexpanthenol is quickly oxidized to pantothenate (pantothenic acid). 
Defficiency of Vitamin B5 results in many dermatological disorder. 
Due to the fact that only Dexpanthenol is converted to Vitamin B5 and not L-Panthenol, the racemic mixture of D- and L- panthenol (DL-panthenol) has only half of the physiological activity of the D-Panthenol. 

These include stimulation of epithelisation, wound healing effect and anti-infl ammatory effect. 
Dexpanthenol is FDA approved for cosmetic use and comes either in D form, or as a racemic mixture. 
Dexpanthenol is also in the FDA list of over-the-counter drug products that are not generally recognized as safe and effective or are misbranded: as "Insect Bite and Sting Drug Products" and "Poison Ivy, Poison Oak, and Poison Sumac Drug Products".

Dexpanthenol is a medication used as a moisturizer to treat or prevent dry, rough, flaky, itchy skin and minor skin irritations (e.g., diaper rash, burns from radiation therapy).
Dry skin is caused by a loss of water in the top layer of the skin. 
Dexpanthenol works by forming an oily layer on the top of the skin that retains water in the skin.

Dexpanthenol Chemical Properties
Melting point: 64～69℃
Alpha: 30.5 º (c=5, H2O on anh. sub)
Boiling point: 118-120 °C (2.7 mmHg)
Density: 1.20 g/mL at 20 °C (lit.)
Vapor pressure: 0Pa at 25℃
Refractive index: 1.495-1.502
Fp: 118-120°C/0.02m
Storage temp.: 2-8°C
Solubility: DMSO (Sparingly), Methanol (Slightly), Water (Sparingly)
Pka: 13.03±0.20(Predicted)
Form: Viscous Liquid or Semi Solid
Color: Clear colorless to slightly yellow
PH: pH (100g/l,25℃) : 8.5～10.5
Optical activity: [α]20/D +30±1°, c = 5% in H2O
Water Solubility: soluble
Sensitive: Hygroscopic
Merck: 14,2947
BRN: 1724947
InChIKey: SNPLKNRPJHDVJA-ZETCQYMHSA-N
LogP: -1.06 at 22℃
CAS DataBase Reference: 81-13-0(CAS DataBase Reference)
NIST Chemistry Reference: Dexpanthenol(81-13-0)
EPA Substance Registry System: (+)-Panthenol (81-13-0)

Dexpanthenol 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. 
Dexpanthenol 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.

Uses    
Dexpanthenol may be used as an analytical reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques as well as partial least-squares multivariate calibration.
Dexpanthenol is an analogue of pantothenic acid (P190300), a member of the B complex vitamins. 
Dexpanthenol is the biologically active enantiomer of Panthenol.

Dexpanthenol is used in many topical products to treat, prevent and relieve itchy, rough, scaly skin and minor skin irritations. 
One of the great benefits of dexpanthenol is that it doesn’t just treat dry skin, it helps to make it more resilient by strengthening the skin’s natural microbiome balance. 
So Dexpanthenol not only gives comfort to dry, dull skin, it strengthens and supports the skin’s moisture barrier, stimulating skin regeneration and promoting healing. 

Dexpanthenol creams use the power of dexpanthenol to lock-in moisture to target even the driest of skin. 
As dexpanthenol is able to penetrate the skin quickly, dexpanthenol creams can provide almost instant deep moisturisation and relief.
Dexpanthenol’s ability to provide supercharged hydration with the power to regenerate the epidermal barrier means it can be used to treat conditions including:

1-Flakey, cracked skin
2-Tight skin
3-Eczema 
4-Itchy, irritated skin 
5-Minor wounds
6-Stings and bites
7-Minor skin irritations. 
8-Nappy rash

This medication is used as a moisturizer to treat or prevent dry, rough, scaly, itchy skin and minor skin irritations (such as diaper rash, skin burns from radiation therapy). 
Emollients are substances that soften and moisturize the skin and decrease itching and flaking. Some products (such as zinc oxide, white petrolatum) are used mostly to protect the skin against irritation (such as from wetness).
Dry skin is caused by a loss of water in the upper layer of the skin. 
Emollients/moisturizers work by forming an oily layer on the top of the skin that traps water in the skin. 

Petrolatum, lanolin, mineral oil and dimethicone are common emollients. 
Humectants, including glycerin, lecithin, and propylene glycol, draw water into the outer layer of skin. 
Many products also have ingredients that soften the horny substance (keratin) that holds the top layer of skin cells together (including urea, alpha hydroxy acids such as lactic/citric/glycolic acid, and allantoin). 
This helps the dead skin cells fall off, helps the skin keep in more water, and leaves the skin feeling smoother and softer.

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

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

Dexpanthenol binds to the hair shaft readily, so, it is a common component of commercial shampoos and hair conditioners (in concentrations of 0.1–1%). 
Dexpanthenol coats the hair and seals its surface, lubricating the hair shaft and giving it a shiny appearance.
Dexpanthenol is also recommended by tattoo artists as a post-tattooing moisturising cream.

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

Dexpanthenol 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. 
The pharmacological mode of action of the drug is unknown. 
Pharmacokinetics data in humans is unavailable.

Manufacturing Process    
130 parts by weight of d(-)-α-hydroxy-β,β-dimethyl-gamma-butyric acid lactone are dissolved in 150 parts by volume of methyl alcohol. 
75 parts by weight of 3-hydroxypropylamine are added, in one portion, to the solution and the mixture is well stirred. 
While the reaction sets in, the temperature of the mixture gradually rises by itself to about 50°C and then drops again after about two hours. 
To cause completion of the reaction, the mixture is allowed to stand at room temperature for 24 hours. 
The so obtained (d+)-α,γdihydroxy-β,β-dimethyl-butyric-acid-(3'-hydroxypropyl)-amide is freed from methyl alcohol in vacuo. 
Dexpanthenol is a colorless, viscous oil, easily soluble in water. 
Dexpanthenol boils under a pressure of 0.02 mm between 118° and 120°C.

Biochem/physiol 
Actions    Dexpanthenol is the alcohol analogue and biological precursor of D-pantothenic acid. These analogues are precursors in the biosynthesis of coenzyme A. 
Dexpanthenol and D-Pantothenic acid are used in a variety of skin protection products. 
Dexpanthenol acid may have a role in controlling keratinocyte proliferation and differentiation.
Dexpanthenol may be used for studies of skin protection emulsions from UV irradiation and as a humectant.

Contact allergens    
Dexpanthenol is the alcohol corresponding to pantothenic acid, of the vitamin B5 group. 
Dexpanthenol is used as a food additive, and in skin and hair products as a conditioning agent. 
Contact dermatitis and urticaria have been reported.

Veterinary Drugs and Treatments    
Dexpanthenol has been suggested for use in intestinal atony or distension, postoperative retention of flatus and feces, prophylaxis and treatment of paralytic ileus after abdominal surgery or traumatic injuries, equine colic (not due to mechanical obstruction) and any other condition when there is an impairment of smooth muscle function. 
Controlled studies are lacking with regard to proving the efficacy of the drug for any of these indications.

Synonyms
Dexpanthenol
D-Panthenol
81-13-0
Pantothenol
Ilopan
D-Pantothenyl alcohol
Bepanthen
Pantol
Bepanthene
Bepantol
(+)-Panthenol
Provitamin B
Motilyn
Panadon
Panthoderm
Thenalton
Zentinic
d-Pantothenol
Pantothenyl alcohol
Cozyme
D-P-A Injection
D(+)-Panthenol
Pantenyl
Synapan
Urupan
D(+)-Pantothenyl alcohol
Intrapan
d panthenol
D-Panthenol 50
Provitamin B5
(2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Pantothenylol
Dexpantenol
(R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Dextro pantothenyl alcohol
Propanolamine, N-pantoyl-
Dexpanthenolum
Alcopan-250
Penthenol
Varitan
N-Pantoyl-propanolamine
Panthenol (D)
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (2R)-
Panthenol (JAN)
Prestwick_529
Dexpanthenol (1.20 g/mL)
Ilopan (TN)
D-(+)-Panthenol
Panthenol, (+)-
D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
N-Pantoyl-3-propanolamine
NSC 302962
D-(+)-Pantothenyl alcohol
1O6C93RI7Z
CHEBI:27373
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)-
Pro-itamin B5
Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)-
component of Pantho-F
NCGC00142622-03
PANTHENOL [JAN]
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide, (R)-
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide, D-(+)-
Panthenolum
Pantenol
Pantenolo
Sinecort
(R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
d(+)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide
component of Zentinic
Pantothenol, D-
Alcool DL-pantotenilico
(+-)-Pantothenyl alcohol
DEXPANTHENOL [USAN]
Dexpantenol [INN-Spanish]
Dexpanthenolum [INN-Latin]
UNII-1O6C93RI7Z
(R)-2,4-Dihydroxy-3,3-dimethylbutyric 3-hydroxypropylamide
Dexpanthenol;
CCRIS 3947
HSDB 296
NSC302962
Fancol DL
NSC-302962
CAS-81-13-0
NCGC00186658-01
Dexpanthenol [USAN:USP:INN:BAN]
EINECS 201-327-3
Dexpanthenol (USP)
MFCD00065006
CORNERGEL
DOLOBENE
BAY 81-2996
BRN 1724947
Panthenol, (+ )-
PANTHENOL 50W
Prestwick0_000022
Prestwick1_000022
Prestwick2_000022
Prestwick3_000022
Dexpanthenol (USP/INN)
DEXPANTHENOL [MI]
D-Panthenol USP/BP/IP
compnent of ilopan-Choline
DEXPANTHENOL [FCC]
DEXPANTHENOL [INN]
bmse000445
PANTHENOL, (R)-
DEXPANTHENOL [HSDB]
EC 201-327-3
ALCOPAN 250
D-PANTHENOL [VANDF]
DEXPANTHENOL [VANDF]
SCHEMBL15861
BSPBio_000083
DEXPANTHENOL [MART.]
4-04-00-01652 (Beilstein Handbook Reference)
DEXPANTHENOL [USP-RS]
DEXPANTHENOL [WHO-DD
SPBio_002004
BPBio1_000093
CHEMBL1200979
Dexpanthenol - USP/FCC Kosher
DTXSID3022906
SCHEMBL20553090
DEXPANTHENOL [ORANGE BOOK]
HMS1568E05
HMS2094E09
HMS2095E05
HMS3712E05
DEXPANTHENOL [EP MONOGRAPH]
(R)-2,4-Dihydroxy-N-(3-hydroxy-propyl)-3,3-dimethylbutanamide
HY-B1391
ZINC1530303
D-Panthenol, >=98.0% (NT)
DEXPANTHENOL [USP MONOGRAPH]
Tox21_111563
LMFA08020198
s4695
AKOS015841507
AKOS015901947
Calcium D-Pantothenate USP/BP/EP/IP
D(+)-alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide
Tox21_111563_1
CCG-213429
CS-8175
DB09357
alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide, D-(+)-
NCGC00142622-01
NCGC00142622-04
AS-14732
D-Panthenol 10 microg/mL in Acetonitrile
Dexpanthenol, tested according to Ph.Eur.
SBI-0206936.P001
D-Panthenol, Vetec(TM) reagent grade, 98%
P0692
C05944
D00193
D70909
EN300-7414583
Q-201048
Q47495755
A6CF1A81-5B98-4C28-A379-EA28FA9DD210
(R)-3-(2,4-Dihydroxy-3,3-dimethylbutyramido)-1-propanol
Dexpanthenol, European Pharmacopoeia (EP) Reference Standard
(2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-butanamide
(R)-()-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
(R)-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-hydroxypropyl)-butanamide
(R)-2,4-Dihydroxy-N-(3-hydroxy-propyl)-3,3-dimethyl-butyramide
D-(+)-2,4-Dihydroxy-3,3-dimethyl-N-(3-hydroxypropyl)butyramide
D-Panthenol, >=98% (perchloric acid titration), >=98% (TLC)
Dexpanthenol, United States Pharmacopeia (USP) Reference Standart
(D)-(+)-2, 4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (theta)-
D(+)-.ALPHA.,.GAMMA.-DIHYDROXY-N-(3-HYDROXYPROPYL)-.BETA.,.BETA.-DIMETHYLBUTYRAMIDE
Dexpanthenol, Pharmaceutical Secondary Standard; Certified Reference Material
1113-70-8