docosan-1-ol

• ChemBase ID: 514
• Molecular Formular: C22H46O
• Molecular Mass: 326.60004
• Monoisotopic Mass: 326.35486609
• SMILES: OCCCCCCCCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCO
• InChI: InChI=1S/C22H46O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h23H,2-22H2,1H3
• InChIKey: NOPFSRXAKWQILS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: docosan-1-ol
• IUPAC Systematic name: Docosan-1-ol
• IUPAC Traditional name: docosanol
• Brand Name: Abreva
• Synonyms: Behenyl alcohol; docosanol; Docosanol; BEHENYL ALCOHOL TECHNICAL GRADE; Behenic alcohol; Cachalot BE-22; n-Docosanol; Docosyl alcohol; Emery 3304; Loxiol VPG 1451; Abreva; 1-Docosanol; BEHENYL ALCOHOL; 1-Docosanol; Docosan-1-ol; 山嵛醇; 正二十二醇

Database IDs

• CAS Number: 30303-65-2; 661-19-8
• EC Number: 211-546-6
• MDL Number: MFCD00002939
• Beilstein Number: 1770470
• PubChem SID: 24850264; 24867521; 46508049; 160963977
• PubChem CID: 12620
• CHEBI ID: 31000
• ATC CODE: D06BB11
• CHEMBL: 1200453
• Chemspider ID: 12100
• DrugBank ID: DB00632
• KEGG ID: D03884
• MeSH Name: docosanol
• Unique Ingredient Identifier: 9G1OE216XY
• Wikipedia Title: Docosanol

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.843943
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 8.807558
• LogD (pH = 7.4): 8.807558
• Log P: 8.807558
• Molar Refractivity: 104.9529 cm^3
• Polarizability: 41.941555 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 9.31
• LOG S: -7.22
• Solubility (Water): 1.96e-05 g/l

PROPERTIES

Physical Property

• Melting Point: 65-72 °C(lit.); 69.85°C (343K); 70-71 °C
• Boiling Point: 179.85°C (453K) (at 29 Pa); 180 °C/0.22 mmHg(lit.)
• Partition Coefficient: 10.009
• Hydrophobicity(logP): 9

Safety Information

• Storage Condition: -20°C
• RTECS: JR1315000
• German water hazard class: nwg
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Topical
• Legal Status: OTC (US)
• Pregnancy Category: B (US)

Product Information

• Purity: ~98%; ≥97.0% (GC); 80%; 95+%; 98%
• Grade: purum; TECHNICAL
• Salt Data: Free Base
• Linear Formula: CH3(CH2)21OH

DETAILS

MP Biomedicals - 05204154

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05213459

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156476

(1-Docosanol)
Purity: ∼98%

DrugBank - DB00632

• Drug Groups: approved; investigational
• Description: Docosanol is a drug used for topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters). A saturated 22-carbon aliphatic alcohol, docosanol exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol inhibits fusion between the plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication.
• Indication: For the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters).
• Pharmacology: Docosanol is a saturated 22-carbon aliphatic alcohol which exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol speeds the healing of cold sores and fever blisters on the face or lips. It also relieves the accompanying symptoms, including tingling, pain, burning, and itching. Docosanol cannot, however, prevent cold sores or fever blisters from appearing.
• Toxicity: Symptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.
• Affected Organisms: Herpes simplex virus
• Absorption: Topical absorption has been shown to be minimal under conditions reflecting normal clinical use.
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1637

Research Area: Infection
Biological Activity:
Docosanol is a saturated fatty alcoholused traditionally as an emollient, emulsifier, and thickener in cosmetics, nutritional supplement (as an individual entity and also as a constituent of polyicosanol). [1] It works by inhibiting fusion between the human cell plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication. Unlike other cold-sore antivirals, docosanol does not act directly on the virus, and as such it is unlikely it will produce drug resistant mutants of HSV. The ED50 of 1-docosanol is around 2.5 mg/ml for plaque inhibition and 1.7 mg/ml for inhibition of virus production for wild-type and Acv-resistant HSV-2. [2]

Sigma Aldrich - 169102

Packaging
50 g in poly bottle

REFERENCES

• http://en.wikipedia.org/wiki/Docosanol