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Butyl-4-hydroxybenzoat
BUTYL P-HYDROXYBENZOATE · BUTYL 4-HYDROXYBENZOATE · SPF · butyl parabens · Butyl parahydroxybenzoate CRS · P-HYDROXYBENZOIC ACID N-BUTYL ESTER · butoben · solbrolb
Identifikatoren & physikalische Daten
| CAS No. | 94-26-8 |
|---|---|
| Summenformel | C11H14O3 |
| Durchschnittliche Molmasse | 194,23 g/mol |
| Monoisotopische Masse | 194,09429431 g/mol |
| SMILES | CCCCOC(=O)c1ccc(O)cc1 |
| InChIKey | QFOHBWFCKVYLES-UHFFFAOYSA-N |
| PubChem CID | 7184 |
| ChEMBL | CHEMBL459008 |
| ChEBI | CHEBI:88542 |
| EC No. | 202-318-7 |
| DTXSID | DTXSID3020209 |
| Lokaler Name | Butyl-4-hydroxybenzoat |
Chemische & physikalische Eigenschaften
| XLogP | 3,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 171 |
| Stoffklassen | Other Uses -> Preservatives |
| Kosmetika | Cosmetics ingredient -> EmulsifierPreservative/StabilizerCosmetic ingredients (Butylparaben) -> CIR (Cosmetic Ingredient Review) |
| Duftstoffe | Fragrance Ingredient (Butyl p-hydroxy benzoate) -> IFRA transparency List |
| Pestizide | Biocide |
| LogP (Verteilungskoeffizient) | log Kow = 3.573.32 |
| Geruch | Odorless |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Color/Form | Small, colorless crystals or powderCrystalline powderFinely divided solid |
| Löslichkeit | less than 1 mg/mL at 63 °F (NTP, 1992)Crystalline powdersolubility in water: approx 1:125 /Butylparaben calcium salt/solubility in water: approx 1:110 /Butylparaben magnesium salt/In water, 2.07X10+2 mg/L at 20 °CVery slightly soluble in waterSOLUBILITY IN WATER: 0.15 G/100 G @ 80 °CSoluble in DMSO, ethyl acetate, methanol.<0.1 g/100 mL at 17 ºC |
| Flammpunkt | 181 °C181℃ |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 156.00 to 157.00 °C. @ 3.50 mm Hg156-157 °C (3.5 mm Hg)156-157 °C3.5 mm Hg(lit.) |
| Schmelzpunkt | 67-70 °C(lit.) |
| Dichte | 1.28 |
| Dampfdruck | 0.002-0.113Pa at 20-50℃ |
| Brechungsindex | 1.5115 (estimate) |
| FEMA | 2203 | BUTYL P-HYDROXY BENZOATE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pKa 8.5 (Uncertain) |
| Farbe | White to almost white |
| Geruch | very faint phenolic |
| Geruchsart | bland |
| Biologische Quelle | synthetic |
| Merck | 14,1584 |
| JECFA Number | 870 |
| BRN | 1103741 |
| Henry-Konstante | 1.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong alkalies. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PRESERVATIVEFRAGRANCE |
| InChI | 1S/C11H14O3/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7,12H,2-3,8H2,1H3 |
| InChIKey | QFOHBWFCKVYLES-UHFFFAOYSA-N |
| SMILES | CCCCOC(=O)c1ccc(O)cc1 |
| LogP (Verteilungskoeffizient) | 3.57 |
| CAS Datenbank | 94-26-8(CAS DataBase Reference) |
| NIST chemische Informationen | P-hydroxybenzoic acid, n-butyl ester(94-26-8) |
| EPA chemische Informationen | Butylparaben (94-26-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 35.6% (479 of 1344) of reports.DangerH315 (60.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1344 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 4-hydroxy-, butyl esterHazard Traits - Endocrine ToxicityReproductive ToxicityCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)REACH registered substance: butyl 4-hydroxybenzoate (EC: 202-318-7)Substance: Butyl 4-hydroxybenzoateButylparaben: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Parabens: Environment tier II assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include skin sensitivity reactions, contact dermatitis, urticaria and angioedema. It can cause skin and eye irritation. Dilute solutions of this type of compound may be painful and cause irritation when applied to the eye. |
| Gefahrenübersicht | Parabens are an uncommon cause of allergic contact dermatitis[Marks, p. 115] A skin irritantCauses liver injury in feeding studies of mice[HSDB] A skin and eye irritantA potential skin sensitizer[CAMEO] An eye and mild skin irritantMay cause skin sensitization[eChemPortal: ERMA] Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin. [Kanerva, p. 1822-3] |
Anwendungen & Verwendung
Beschreibung
Butylparaben is an antimicrobial agent used in pharmaceutical suspensions. It is act by inhibiting DNA, RNA, and enzymes (eg, ATPase and phosphotransferase) synthesis. Butylparaben may be used alone or with other parabens, chiefly methylparaben and/or propylparaben, in medications. It is common in many liquid and solid (gel cap) OTC products such as Tylenol, Drixoral, Maalox, and Mylanta. Unfortunately, butylparaben concentrations were seldom identified for OTC or prescription products. No attempt was made to identify butylparaben-containing dietary supplements.
Herstellung & Synthese
synthetische
Butyl paraben is prepared by esterifying p-hydroxybenzoic acid with butyl alcohol in the presence of an acid catalyst, such as sulfuric acid, and an excess of the specific alcohol.