Salicylaldehyd
2-HYDROXYBENZALDEHYDE · SALICYLIC ALDEHYDE · salicyaldehyde · salicyladehyde · O-HYDROXYBENZALDEHYDE · FEMA 3004 · 2-hydroxy-benzaldehyd · SALICYLALDEHYD
Identifikatoren & physikalische Daten
| CAS No. | 27761-48-4 |
|---|---|
| Summenformel | C7H6O2 |
| Durchschnittliche Molmasse | 122,12 g/mol |
| Monoisotopische Masse | 122,03677943 g/mol |
| SMILES | O=Cc1ccccc1O |
| InChIKey | SMQUZDBALVYZAC-UHFFFAOYSA-N |
| PubChem CID | 6998 |
| ChEMBL | CHEMBL108925 |
| ChEBI | CHEBI:16008 |
| EC No. | 201-961-0 |
| DTXSID | DTXSID1021792 |
| Lokaler Name | Salicylaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 101 |
| Stoffklassen | Other Classes -> Benzaldehydes |
| Kosmetika | Cosmetics ingredient -> Fragrance |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Duftstoffe | Fragrance Ingredient (Salicylaldehyde) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 1.811.62 |
| Geruch | Bitter, almond-like odorPungent, irritating odor similar to benzenaldehyde, acetophenone, and nitrobenzene, but with phenolic notes |
| Geschmack | Nut-like, coumarin flavor at low levelsBurning taste |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.1674 at 68 °F (USCG, 1999) - Denser than waterwill sink1.167 g/cu cm at 20 °C/4 °C1.159-1.1701.167 @25 °C1.146 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | Dynamic viscosity = 2.50X10-3 Pa.s at 25 °C |
| Color/Form | LiquidColorless, oily liquid or dark-red oilColorless to straw, oily liquid |
| Schmelzpunkt | 1-2 °C (lit.) |
| Siedepunkt | 197 °C (lit.) |
| Dampfdichte | 4.2 (vs air) |
| Dampfdruck | 1 mm Hg ( 33 °C) |
| Brechungsindex | n20/D 1.573(lit.) |
| FEMA | 3004 | SALICYLALDEHYDE |
| Flammpunkt | 170 °F |
| Lagerbedingungen | -20°C |
| Löslichkeit | 4.9g/lslightly soluble |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 8.37(at 25℃) |
| Farbe | Clear yellow |
| pH | 6-8 (H2O, 20℃)Not applicable |
| Geruch | Bitter almonds |
| Geruchsart | medicinal |
| Biologische Quelle | synthetic |
| Spezifische Wärmekapazität | Cp(liquid): 1.82 J/(g·K), at 25℃ |
| JECFA Number | 897 |
| Merck | 14,8326 |
| BRN | 471388 |
| Henry-Konstante | 1.1×100 mol/(m3Pa) at 25℃, Ji et al. (2008) |
| Dielektrizitätskonstante | 13.9(20℃) |
| Stabilität | Stable. Combustible. Incompatible with strong bases, strong reducing agents, strong acids, strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCE |
| InChI | 1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H |
| InChIKey | SMQUZDBALVYZAC-UHFFFAOYSA-N |
| SMILES | Oc1ccccc1C=O |
| LogP (Verteilungskoeffizient) | 1.66 at 25℃ and pH6.2-6.3 |
| CAS Datenbank | 90-02-8(CAS DataBase Reference) |
| NIST chemische Informationen | Benzaldehyde, 2-hydroxy-(90-02-8) |
| EPA chemische Informationen | Salicylaldehyde (90-02-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3872 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Benzaldehyde, 2-hydroxy-Hazard Traits - Fragrance AllergenCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzaldehyde, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 2-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 28-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/57152-Hydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Can react with oxidizing materials. (USCG, 1999) |
| Brandpotenzial | Flamable when exposed to heat or flame. |
| Gesundheitsgefahren | LIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999) |
| Gefahrenübersicht | A skin and eye irritant[CAMEO] A skin irritant[eChemPortal: ERMA] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] An irritantCan be absorbed through skin[MSDSonline] |
| FDA-Anforderungen | Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Salicylaldehyde is included on this list. |
Anwendungen & Verwendung
Beschreibung
Flüssigkeit von charakteristischem Geruch. Mit Wasserdämpfen flüchtig. Schwer löslich in Wasser, mischbar mit Alkohol, Ether und Chloroform. Sdp.: 197� C. NULL
Beschreibung
Salicylaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless or pale yellow liquid with a bitter almond odor and a burning taste. It is soluble in alcohol, benzene, and ether, and very slightly soluble in water. Salicylaldehyde is found in shrubs of the genus Spiraea and is usually produced from phenol by the action of chloroform in the presence of an alkali base. It is used in the production of coumarin, saligenin, and salicylaldoxime (an important analytical reagent), and also in analytical chemistry—for example, to detect hydrazine. Besides, salicylaldehyde is a key precursor to various chelating agents and a flavouring ingredient.
Occurrence
Occurs frequently in nature; in the flowers of Spirea ulmaria and other Spireae, in the roots of Crepis foetida L., in the fruits of Pinus avium, in the rind of Rauqolfia caffra, in the leaves of Ceanothus velutinus and in the essential oil of Cinnamomum cassia and of tobacco leaves. Also reported found in grapes, tomato, baked potato, cinnamon bark, cassia leaf, peppermint oil, pennyroyal oil, parmesan cheese, butter, milk powder, roasted chicken, beer, rum, Japanese whiskey, sherry, coffee, tea, soybean, mushroom, buckwheat, Bourbon vanilla, Chinese quince, Muscat grape, vanilla and mastic gum oil.
Herstellung & Synthese
synthetische
Salicylaldehyde is synthesized from phenol, chloroform, and alkali according to the Reimer–Tiemman method, which was developed in 1876. starting material for the manufacture of coumarin.