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81-13-0

Basic Information
CAS No.: 81-13-0
Name: Dexpanthenol
Molecular Structure:
Molecular Structure of 81-13-0 (Dexpanthenol)
Formula: C9H19NO4
Molecular Weight: 205.25
Synonyms: Butanamide,2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)-;Butyramide,2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)- (8CI);(+)-Panthenol;Alcopan 250;Bepanthen;Bepanthene;Cornergel;Cozyme;D(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide;D(+)-Panthenol;D(+)-Pantothenyl alcohol;D(+)-a,g-Dihydroxy-N-(3-hydroxypropyl)-b,b-dimethylbutyramide;D-Panthenol;D-Pantothenyl alcohol;Butanamide,2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (2R)-;Dolobene;Ilopan;Intrapan;Motilyn;Panadon;Pantenyl;Panthenol 50W;Panthenol, (+)-;Pantol;Pantothenyl alcohol;Provitamin B;Thenalton;Urupan;Zentinic;d-Pantothenol;
EINECS: 201-327-3
Density: 1.166 g/cm3
Melting Point: 64~69℃
Boiling Point: 483.6 °C at 760 mmHg
Flash Point: 246.3 °C
Solubility: Soluble in water
Appearance: clear colorless to slightly yellow viscous liquid
Hazard Symbols: HarmfulXn
Risk Codes: 36/37/38-48-41-37/38-20/21/22
Safety: 23-24/25-45-36/37/39-26-22
Transport Information:
PSA: 89.79000
LogP: -0.74470
Synthetic route
156-87-6

propan-1-ol-3-amine

599-04-2

(R)-Pantolacton

81-13-0

pantothenol

Conditions
ConditionsYield
With triethylamine In ethanol at 160℃; for 3h; Microwave irradiation;95%
With methanol
at 60℃; for 5h;

A

74561-18-5

dexpanthenol

B

81-13-0

pantothenol

Conditions
ConditionsYield
With LUX i-Amylose-1 In ethanol; hexane at 25℃; Temperature; Resolution of racemate;
81-13-0

pantothenol

371-27-7

2,2,2-trifluoroethylbutyrate

N-(3'-Butanoyloxy)propyl-3,3-dimethyl-2,4-dihydroxybutanamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 42 - 45℃; porcine pancreas lipase;99%
81-13-0

pantothenol

108-24-7

acetic anhydride

3-[[(2R)-2,4-diacetoxy-3,3-dimethylbutanoyl]amino]propyl acetate

Conditions
ConditionsYield
Stage #1: pantothenol; acetic anhydride With dmap at 60 - 90℃; for 2h;
Stage #2: With acetic acid In ethyl acetate at 80 - 110℃; under 7.60051 Torr;
93.2%
With pyridine at 25℃; for 12h; Inert atmosphere;62%
81-13-0

pantothenol

67-64-1

acetone

934244-35-6

(R)-2,2,5,5-tetramethyl-[1,3]dioxane-4-carboxylic acid (3-hydroxypropyl)amide

Conditions
ConditionsYield
Stage #1: pantothenol; acetone With sodium sulfate; toluene-4-sulfonic acid at 20℃;
Stage #2: With sodium hydrogencarbonate In water
93%
With toluene-4-sulfonic acid; sodium sulfate at 20℃; for 4h;59%
Stage #1: pantothenol; acetone With chloro-trimethyl-silane at 20℃; for 3h; Inert atmosphere;
Stage #2: With triethylamine pH=7;
54%
With toluene-4-sulfonic acid at 0 - 20℃; for 72h; Molecular sieve;
81-13-0

pantothenol

2186-92-7

p-Anisaldehyde dimethyl acetal

1196055-91-0

(4R)-N-(3-hydroxypropyl)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamide

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 24h;86%
81-13-0

pantothenol

108-24-7

acetic anhydride

D-panthenyl triacetate

Conditions
ConditionsYield
Stage #1: pantothenol; acetic anhydride at 80℃; for 9h;
Stage #2: With sodium hydroxide
78%
87-51-4

indole-3-acetic acid

81-13-0

pantothenol

3-[[(2R)-2,4-bis[[2-(1H-indol-3-yl)acetyl]oxy]-3,3-dimethylbutanoyl]amino]propyl 2-(1H-indol-3-yl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;78%
81-13-0

pantothenol

359700-09-7

(E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid

tert-butyl 3-[(E)-3-[3-[[(2R)-2,4-bis[[(E)-3-(1-tert-butoxycarbonylindol-3-yl)prop-2-enoyl]oxy]-3,3-dimethylbutanoyl]amino]propoxy]-3-oxoprop-1-enyl]indole-1-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 15℃; for 12h;69%
106-31-0

butanoic acid anhydride

81-13-0

pantothenol

3-[[(2R)-2,4-di(butanoyloxy)-3,3-dimethylbutanoyl]amino]propyl butanoate

Conditions
ConditionsYield
With pyridine at 25℃; for 12h; Inert atmosphere;67%
830-96-6

Indole-3-propionic acid

81-13-0

pantothenol

3-[[(2R)-2,4-bis[3-(1H-indol-3-yl)propanoyloxy]-3,3-dimethylbutanoyl]amino]propyl 3-(1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 12h;43%
81-13-0

pantothenol

116838-41-6

(R)-3-(benzyloxy)-butanoic acid

3-[[(2R)-2,4-bis[[(3R)-3-benzyloxybutanoyl]oxy]-3,3-dimethylbutanoyl]amino]propyl (3R)-3-benzyloxybutanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;19%
81-13-0

pantothenol

[(1R)-3-chloro-1-methyl-3-oxo-propyl] butanoate

3-[[(2R)-2,4-bis[[(3R)-3-butanoyloxybutanoyl]oxy]-3,3- dimethyl-butanoyl]amino]propyl (3R)- 3-butanoyloxybutanoate

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 25℃; for 12h; Inert atmosphere;16%
81-13-0

pantothenol

79-83-4

pantothenic acid

Conditions
ConditionsYield
With barium permanganate; sulfuric acid
im Organismus von Ratten;
81-13-0

pantothenol

112-67-4

n-hexadecanoyl chloride

17097-25-5

(R)-3,3-dimethyl-2,4-bis-palmitoyloxy-butyric acid-(3-palmitoyloxy-propylamide)

Conditions
ConditionsYield
With pyridine; chloroform
38757-64-1

4,8-dimethyl-nona-3t,7-dienoyl chloride

81-13-0

pantothenol

(E)-4,8-Dimethyl-nona-3,7-dienoic acid (R)-3-((E)-4,8-dimethyl-nona-3,7-dienoyloxy)-1-[3-((E)-4,8-dimethyl-nona-3,7-dienoyloxy)-propylcarbamoyl]-2,2-dimethyl-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

36392-06-0

3,7-dimethyl-6-octenoyl chloride

3,7-Dimethyl-oct-6-enoic acid (R)-3-(3,7-dimethyl-oct-6-enoyloxy)-1-[3-(3,7-dimethyl-oct-6-enoyloxy)-propylcarbamoyl]-2,2-dimethyl-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

61899-99-8

2,6,6-trimethyl-2-hexene-1-carbonyl chloride

C29H47NO6

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

58558-13-7

(2E)-3,7-dimethyl-2,6-octadienoyl chloride

(E)-3,7-Dimethyl-octa-2,6-dienoic acid (R)-3-((E)-3,7-dimethyl-octa-2,6-dienoyloxy)-1-[3-((E)-3,7-dimethyl-octa-2,6-dienoyloxy)-propylcarbamoyl]-2,2-dimethyl-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

76936-45-3

5,9,13-trimethyl-tetradeca-4,8,12-trienoyl chloride

(4E,8E)-5,9,13-Trimethyl-tetradeca-4,8,12-trienoic acid (R)-3-hydroxy-2,2-dimethyl-3-[3-((4E,8E)-5,9,13-trimethyl-tetradeca-4,8,12-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

76936-45-3

5,9,13-trimethyl-tetradeca-4,8,12-trienoyl chloride

(4E,8E)-5,9,13-Trimethyl-tetradeca-4,8,12-trienoic acid (R)-2,2-dimethyl-3-((4E,8E)-5,9,13-trimethyl-tetradeca-4,8,12-trienoyloxy)-1-[3-((4E,8E)-5,9,13-trimethyl-tetradeca-4,8,12-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

81790-45-6

geranylacetyl chloride

(E)-5,9-Dimethyl-deca-4,8-dienoic acid (R)-3-((E)-5,9-dimethyl-deca-4,8-dienoyloxy)-1-[3-((E)-5,9-dimethyl-deca-4,8-dienoyloxy)-propylcarbamoyl]-2,2-dimethyl-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

73427-31-3

E,E-farnesic acid chloride

(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoic acid (R)-3-hydroxy-2,2-dimethyl-3-[3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

73427-31-3

E,E-farnesic acid chloride

(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoic acid (R)-2,2-dimethyl-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienoyloxy)-1-[3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

(3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienoyl chloride

(3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienoic acid (R)-3-hydroxy-2,2-dimethyl-3-[3-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

(3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienoyl chloride

(3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienoic acid (R)-2,2-dimethyl-3-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienoyloxy)-1-[3-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienoyloxy)-propylcarbamoyl]-propyl ester

Conditions
ConditionsYield
With pyridine In chloroform Heating;
81-13-0

pantothenol

2212-88-6

2-Cyanoethyl phosphate

2-Hydroxy-4-phosphoryloxy-3,3-dimethyl-N-<3-phosphoryloxy-propyl>-butyramid

Conditions
ConditionsYield
(i) DCC, (ii) aq. NaOH; Multistep reaction;
81-13-0

pantothenol

7664-93-9

sulfuric acid

Ba(MnO4)2

Ba(MnO4)2

79-83-4

pantothenic acid

81-13-0

pantothenol

25561-30-2

N,O-Bis(trimethylsilyl)trifluoroacetamide

TMS-panthenol

Conditions
ConditionsYield
With pyridine at 80℃; for 1h;
81-13-0

pantothenol

100-99-2

triisobutylaluminum

Aluminium panthenolate

Conditions
ConditionsYield
In dichloromethane; toluene
Downstream Products
558-43-0
79-83-4
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    Dexpanthenol D-PANTHENOL 81-13-0 CAS

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    Panthenol Cas. No.: 81-13-0 M.F.: C9H19NO4 M.W.: 205.25 Specifications: Molecular formula: C9H19NO4 Molecular weight : 205.25 Assay: 50% 75% 98% 99% Quality Standards: USP30 or Cosmetic grade Characteristic: Colorless to yellow

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  • Dexpanthenol   CAS: 81-13-0

  • Casno:

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    Description References Product Name: Dexpanthenol Synonyms: 4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-(theta)-butanamid;4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-d-(+)-butyramid;Alcopan-250;Bepanthen;Bepanthene;Bepantol;Butanamide, 2,4-di

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Chemistry

Molecule structure of Dexpanthenol (CAS NO.81-13-0):

IUPAC Name: 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide 
Molecular Weight: 205.25146 g/mol
Molecular Formula: C9H19NO4 
Density: 1.166 g/cm3 
Boiling Point: 483.6 °C at 760 mmHg 
Flash Point: 246.3 °C
Index of Refraction: 1.501
Molar Refractivity: 51.89 cm3
Molar Volume: 175.9 cm3
Surface Tension: 49.1 dyne/cm 
Enthalpy of Vaporization: 86.28 kJ/mol
Vapour Pressure: 2.21E-11 mmHg at 25 °C 
Storage Temp.: −20 °C
Water Solubility: soluble
Sensitive: hygroscopic
XLogP3-AA: -0.9
H-Bond Donor: 4
H-Bond Acceptor: 4
Rotatable Bond Count: 6
Tautomer Count: 2
Exact Mass: 205.131408
MonoIsotopic Mass: 205.131408
Topological Polar Surface Area: 89.8
Heavy Atom Count: 14
Canonical SMILES: CC(C)(CO)C(C(=O)NCCCO)O
InChI: 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
EINECS: 201-327-3
Product Categories: Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts

Uses

 Dexpanthenol (CAS NO.81-13-0) has good skin penetration in ointment. In cosmetics, Dexpanthenol is a humectant, emollient and moisturizer. It is also used as pharmaceutical intermediates.

Toxicity Data With Reference

1.    

skn-rbt 500 mg/4H MLD

    JACTDZ    Journal of the American College of Toxicology. 6 (1)(1987),139.
2.    

eye-rbt 500 µg MLD

    JACTDZ    Journal of the American College of Toxicology. 6 (1)(1987),139.
3.    

orl-mus LD50:15 g/kg

    JACTDZ    Journal of the American College of Toxicology. 6 (1)(1987),139.
4.    

ipr-mus LD50:9 g/kg

    FRPSAX    Farmaco, Edizione Scientifica. 14 (1959),43.
5.    

ivn-mus LD50:7000 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),599.
6.    

ivn-rbt LD50:4000 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),599.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 36/37/38-48-41-37/38-20/21/22 
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 the eyes. 
R37/38:Irritating to respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 23-24/25-45-36/37/39-26-22 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S22:Do not breathe dust.
WGK Germany: 1
RTECS: ES4316000
F: 3-10
Moderately toxic by intravenous route. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.

Specification

 Dexpanthenol (CAS NO.81-13-0) is also named as (+)-Panthenol ; (R)-2,4-Dihydroxy-N-(3-hydroxy-propyl)-3,3-
dimethylbutanamide ; 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide ; (R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide, D-(+)- ; 4-04-00-01652 (Beilstein Handbook Reference) ; Alcopan-250 ; BAY 81-2996 ; BRN 1724947 ; Bepanthen ; Bepanthene ; D(+)-Pantothenyl alcohol ; D(+)-alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide ; D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide ; D-P-A Injection ; Intrapan ; Motilyn ; NSC 302962 ; Panadon ; Pantenyl ; Thenalton ; UNII-1O6C93RI7Z ; Urupan ; Varitan ; Zentinic ; alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide, D-(+)- ; d(+)-Panthenol ; d-Pantothenol ; d-Pantothenyl alcohol . Dexpanthenol (CAS NO.81-13-0) is clear colorless to slightly yellow viscous liquid. It is soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin.

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