| Identification | More | [Name]
Panthenol | [CAS]
16485-10-2 | [Synonyms]
(+/-)-2,4-DIHYDROXY-3,3-DIMETHYLBUTYRIC 3-HYDROXY-PROPYLAMIDE
2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYLBUTYRAMIDE
3-(2,4-DIHYDROXY-3,3-DIMETHYLBUTYRAMIDO)-1-PROPANOL
DL-2 4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3 3-DIMETHYLBUTYRAMIDE
DL-N-PANTOYL-E-PROPANOLAMINE
DL-PANTHENOL
DL-PANTOTHENOL
DL-PANTOTHENYLOL
LABOTEST-BB LT00244791
(+/-)-PANTHENOL
PANTHENOL
PANTOTHENOL
(+/-)-PANTOTHENYL ALCOHOL
2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-,(+-)-Butanamide
4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-(+-)-butanamid
4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-(+-)-butyramid
4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-(+/-)-butanamid
4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-dl-butyramid
alcooldl-pantotenilico
pantenol | [EINECS(EC#)]
240-540-6 | [Molecular Formula]
C9H19NO4 | [MDL Number]
MFCD00002944 | [Molecular Weight]
205.25 | [MOL File]
16485-10-2.mol |
| Questions And Answer | Back Directory | [General Description]
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.
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.
| [Uses]
Panthenol, 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.
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. The vitamin ingredient Panthenol is valued in skin and hair care applications for its moisturizing properties. It has anti-inflammatory effects and soothes irritated and sensitive skin. For hair care application it is known for its humectant properties and its ability to improve the resistance of hair to mechanical stress. | [Mechanism of action]
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.
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. | [Side effects]
Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported. Generally, topical panthenol formulations were well tolerated with minimal risk of skin irritation or sensitization. |
| Chemical Properties | Back Directory | [Melting point ]
66-69 °C (lit.) | [alpha ]
0°(c=5, H2O) | [Boiling point ]
118-120 °C(Press: 0.02 Torr) | [density ]
1.166±0.06 g/cm3(Predicted) | [vapor pressure ]
0.004Pa at 25℃ | [storage temp. ]
−20°C
| [solubility ]
Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
13.03±0.20(Predicted) | [color ]
White to Off-White | [Water Solubility ]
Soluble in water, ethanol, ether, chloroform, and propylene glycol. | [Sensitive ]
Hygroscopic | [Merck ]
14,2947 | [BRN ]
1724945 | [Cosmetics Ingredients Functions]
HAIR CONDITIONING
ANTISTATIC
SKIN CONDITIONING | [Cosmetic Ingredient Review (CIR)]
Panthenol (16485-10-2) | [InChI]
1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14) | [InChIKey]
SNPLKNRPJHDVJA-UHFFFAOYSA-N | [SMILES]
CC(C)(CO)C(O)C(=O)NCCCO | [LogP]
-1.02 at 22℃ | [Uses]
panthenol (pro-vitamin B5) acts as a penetrating moisturizer. Panthenol appears to stimulate cellular proliferation and aid in tissue repair. Studies indicate that when topically applied, panthenol penetrates the skin and gets converted into pantothenic acid, a B complex vitamin. Such action could possibly influence the skin’s natural resources of pantothenic acid. It imparts a nonirritant, non-sensitizing, moisturizing, and conditioning feel and promotes normal keratinization and wound-healing. Panthenol protects the skin against sunburn, provides relief for existing sunburn, and enhances the natural tanning process. Panthenol’s humectant character enables it to hold water in the product or attract water from the environment, resulting in a moisturizing effect. It enhances skin suppleness, and claims are that it also acts as an anti-inflammatory agent. It is considered a non-comedogenic raw material. | [CAS DataBase Reference]
16485-10-2(CAS DataBase Reference) | [EPA Substance Registry System]
16485-10-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R48:Danger of serious damage to health by prolonged exposure.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37:Wear suitable gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
ES4316500
| [F ]
3 | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29362400 | [Storage Class]
11 - Combustible Solids | [Toxicity]
mouse,LD50,intraperitoneal,10100mg/kg (10100mg/kg),Farmaco, Edizione Scientifica. Vol. 14, Pg. 43, 1959. |
| Hazard Information | Back Directory | [Application]
Panthenol is used as a moisturizer, soothing and softening agent.- Skin care: It improves hydration and elasticity of the
skin, reduces itching and inflammation of the skin, improves skin
elasticity, and accelerates the rate of healing of wounds. In topical
creams, it is found to be in a concentration of 1-5%.
- Hair care: 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,
lubricating the hair shaft and giving it a shiny appearance. It can also
help protect your hair from styling or environmental damage by locking
in moisture.
| [Flammability and Explosibility]
Nonflammable | [Synthesis]
Panthenol [D(+)-panthenol, α,γ-dihydroxy-N-(3-hydroxypropyl)-β,β-dimethylbutyramide] is synthesized by condensation of D-pantolactone (II) with 3-aminopropyl alcohol (III) in a medium of the lowest aliphatic alcohol: 3-aminopropyl alcohol (4.61 g, 0.062 mol, ca. 5% excess) was added to a solution of D-pantolactone (7.61 g, 0.058 mol) in ethanol (30 ml) and stirred at 78–80°C for 2 h (second-order reaction); after cooling to 20°C, KU-23 sulfonate-type cation-exchange resin (1.5 g) was added and stirred for 30 min to remove residual amino alcohol, the resin was filtered off and washed with ethanol (15 ml), and the combined filtrate was evaporated to dryness at 60–65°C to give chromatographically pure D-panthenol in 98.6% yield. Optimization studies showed that with equimolar reactants, 90.17% of 3-aminopropanol reacted after 2 h at 70°C in methanol and 94.7% of panthenol formed after 2 h at 80°C in ethanol; with a 5% excess of 3-aminopropanol, 99.6% D-panthenol was formed after 2 h at 80°C [1]. | [storage]
Store at -20°C | [References]
[1] KOZLOVA, G. S., EROKHINA, T. I., & GUNAR, V. I. (1977). ChemInform Abstract: SYNTHESIS OF D(+)-PANTHENOL. ChemInform, 8 38. https://doi.org/10.1002/chin.197738363 |
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