p-Anissure

Bezeichnung:p-Anissure

CAS-Nr100-09-4

Englisch Name:4-Methoxybenzoic acid

CBNumberCB6746524

SummenformelC8H8O3

Molgewicht152.15

MOL-Datei100-09-4.mol

Synonyma

p-Anissure

p-Anissure physikalisch-chemischer Eigenschaften

Schmelzpunkt	182-185 °C(lit.)
Siedepunkt	275 °C
chüttdichte	380kg/m3
Dichte	1.385
Dampfdruck	0.001Pa at 25℃
Brechungsindex	1.571-1.576
FEMA	3945 \| 4-METHOXYBENZOIC ACID
Flammpunkt	185 °C
storage temp.	Store below +30°C.
Löslichkeit	H2O: soluble2500 parts
pka	4.50(at 25℃)
Aggregatzustand	Powder
Farbe	White to slightly gray-beige
PH	3-4 (0.3g/l, H2O, 20℃)
Geruch (Odor)	at 10.00 % in dipropylene glycol. faint putrid sweet cadaverous
Geruchsart	animal
Biologische Quelle	synthetic
Wasserlöslichkeit	Soluble in water at 20°C 0.3g/L. Soluble in alcohol, ethyl acetate and ether.
Merck	14,666
JECFA Number	883
BRN	508910
Henry's Law Constant	1.8×10³ mol/(m³Pa) at 25℃, Abraham and Jr. (2019)
Stabilität	Stable. Incompatible with strong oxidizing agents.
Major Application	food and beverages pharmaceutical
Kosmetik-Inhaltsstoffe Funktionen	FRAGRANCE
InChI	1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
InChIKey	ZEYHEAKUIGZSGI-UHFFFAOYSA-N
SMILES	COc1ccc(cc1)C(O)=O
LogP	1.96
CAS Datenbank	100-09-4(CAS DataBase Reference)
NIST chemische Informationen	Benzoic acid, 4-methoxy-(100-09-4)
EPA chemische Informationen	Benzoic acid, 4-methoxy- (100-09-4)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-22
S-Sätze:	26-36-24/25
WGK Germany	1
RTECS-Nr.	BZ4395000
Selbstentzündungstemperatur	185 °C
Hazard Note	Irritant
TSCA	TSCA listed
HS Code	29189090
Speicherklasse	13 - Non Combustible Solids
Toxizität	LD50 orally in Rabbit: > 5000 mg/kg

Gefahreninformationscode (GHS)

4-Methoxybenzoic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
P-Anisic acid, also known as 4-Methoxybenzoic acid or draconic acid, is an organic acid that has a sweet flavor. It is one of the isomers of anisic acid, including m-anisic acid and o-anisic acid. The term "anisic acid" often refers to this form specifically. P-anisic acid is produced through the oxidation of p-cresyl-methyl ether.
Chemische Eigenschaften
It appears as a colorless needle crystal at room temperature. It is soluble in ethanol, ether, and chloroform, and only slightly soluble in hot water. It remains insoluble in cold water. It is used as an intermediate for aniracetam, as well as a preservative and fragrance.
Verwenden
4-Methoxybenzoic acid (p-Anisic acid) is used in oxidation and reduction of cytochrome c in solution through different self-assembled monolayers on gold electrodes using cyclic voltammetry. p-Anisic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds.
Definition
ChEBI: 4-methoxybenzoic acid is a methoxybenzoic acid substituted with a methoxy group at position C-4. It has a role as a plant metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate.
synthetische
To obtain 4-Methoxybenzoic acid, the mole ratio of cobalt and manganese is modified and p-methoxy toluene is reacted with oxygen or an oxygen-containing gas in the presence of acetic acid. The following is the experimental procedure:1. Using n-hexyl bromide, tri (n-hexyl) amine, para-methoxy toluene with cobalt chloride hexahydrate in about 9h;
2. By a catalytic oxidation process using p-methoxy toluene and propionic acid over a catalyst comprising of CoBr2.6H2O and MnBr2.4H2O with a reaction time of 20h;
3. Through changing the mole ratio of cobalt and manganese, using p-methoxy toluene with oxygen or oxygen containing gas in the presence of acetic acid to obtain the product.
Synthesis Reference(s)
Journal of Heterocyclic Chemistry, 25, p. 973, 1988 DOI: 10.1002/jhet.5570250351
Tetrahedron Letters, 34, p. 4603, 1993 DOI: 10.1016/S0040-4039(00)60635-4
Allgemeine Beschreibung
4-Methoxybenzoic acid is the sole source of carbon and energy for growth in the cultures of Nocardia sp. DSM 1069. It is effective in clearing congestion in the lungs and the respiratory tracts in conditions like asthma or bronchitis.
Reaktivität anzeigen
4-Methoxybenzoic acid belongs to Aromatic acid hydrazides (Others include isonicotinic, benzoic, and salicylic). The reaction of thiosemicarbazide and aromatic acid hydrazides with 4H-chromen-4-imines could prepare o-hydroxyphenyl derivatives of 1H-pyrazolethioamides and 1H-pyrazol-5-ylphenols derivatives[4].
Hazard
Thermal decomposition can lead to release of irritating gases and vapors, Carbon monoxide (CO), Carbon dioxide (CO2).
Biochem/physiol Actions
The cytochrome P450 enzyme CYP199A4, a heme-dependent cytochrome P450 (CYP) monooxygenase enzyme, can efficiently demethylate 4-methoxybenzoic acid. Mechanistically, O-demethylation of 4-methoxybenzoic acid occurs via hydrogen abstraction by Compound I, followed by oxygen rebound to give the hydroxylated hemiacetal which spontaneously decomposes to yield 4-hydroxybenzoic acid and formaldehyde[5].
Materials Uses
The reaction of 4-methoxybenzoic acid and substituted tin chlorides gave the corresponding substituted tin complexes. Poly(vinyl chloride) was doped with a small quantity (0.5%) of the tin complexes and homogenous thin films were made. The effects of the additives on the stability of the polymeric material on irradiation with ultraviolet light were assessed using different methods. Such additives act as efficient ultraviolet absorbers, peroxide quenchers, and hydrogen chloride scavengers^[6].
Sicherheitsprofil
Poison by subcutaneous route.When heated to decomposition it emits acrid smoke andirritating vapors.
Solubility in organics
Soluble in alcohol and oils.
läuterung methode
Crystallise p-anisic acid from EtOH, water, EtOH/water or toluene. The S-benzylisothiuronium salt has m 189o (from EtOH). [Beilstein 10 II 91, 10 III 280, 10 IV 346.]
Einzelnachweise
[1] Michael Ash (2004) Handbook of Preservatives
[2] Asim Kumar Mukhopadhyay (2004) Industrial Chemical Cresols and Downstream Derivatives
[3] https://en.wikipedia.org/wiki/P-Anisic_acid
[4] Zahorulko S, et al. Recyclization of 4 H -chromen-4-imine derivatives under the influence of dinucleophiles with the formation of functionally substituted pyrazoles. Monatshefte für Chemie - Chemical Monthly, 2019; 150: 1487–1493.
[5] Coleman T, et al. The importance of the benzoic acid carboxylate moiety for substrate recognition by CYP199A4 from Rhodopseudomonas palustris HaA2. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, 2016; 1864: 667-675.
[6] Hadi, A. G., Baqir, S. J., Ahmed, D. S., El-Hiti, G. A., Hashim, H., Ahmed, A., Kariuki, B. M., Yousif, E. (2021). Substituted Organotin Complexes of 4-Methoxybenzoic Acid for Reduction of Poly(vinyl Chloride) Photodegradation. Polymers. https://doi.org/10.3390/polym13223946

4-Methoxybenzoic acid Upstream-Materialien And Downstream Produkte

p-Anissure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

100-09-4, 4-Methoxybenzoic acid Verwandte Suche:

Send Inquriy