Heptyl 4-hydroxybenzoate

Base Information

• Chemical Name: Heptyl 4-hydroxybenzoate
• CAS No.: 1085-12-7
• Molecular Formula: C14H20 O3
• Molecular Weight: 236.311
• Hs Code.: 29182900
• European Community (EC) Number: 214-115-0
• NSC Number: 309818
• UNII: K2CIJ448IX
• DSSTox Substance ID: DTXSID4022523
• Nikkaji Number: J87.217B
• Wikipedia: Heptylparaben
• Wikidata: Q5732121
• Metabolomics Workbench ID: 46563
• ChEMBL ID: CHEMBL3186719
• Mol file: 1085-12-7.mol

Synonyms:heptylparaben

Chemical Property of Heptyl 4-hydroxybenzoate

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 1.74E-05mmHg at 25°C
• Melting Point: 46-51 ºC
• Refractive Index: 1.514
• Boiling Point: 353.6ºC at 760 mmHg
• PKA: 8.23±0.15(Predicted)
• Flash Point: 143.1ºC
• PSA: 46.53000
• Density: 1.051g/cm3
• LogP: 3.51940
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in alcohol, phenoxyethanol, propylene glycol. Insoluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 236.14124450
• Heavy Atom Count: 17
• Complexity: 208

Purity/Quality:

98%,99%, ^*data from raw suppliers

n-Heptyl4-Hydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCOC(=O)C1=CC=C(C=C1)O
• Description: Hesperidin is one of a large group of bio-flavonoids isolated from citrus fruits. Flavonoids comprise a group of naturally occurring compounds which are among the most ubiquitous in the plant kingdom. The basic flavone structure consists of 1,4-benzopyrone with a phenyl substitution in the 2-position. Flavonoids differ in the number and position of substitutions on the aromatic rings and in the extent and character of oxidation in the pryone portion of the molecule. Hydroxyl groups enable flavonoids to combine with sugars to form glycosides, and it is in this form that the flavonoids are usually found in nature. Glucose is the most common prosthetic group, although other sugars, as well as glucuronic and galacturonic acids, have been identified. Hesperetin is the aglycone remaining following hydrolysis from the prosthetic group.Hesperidin complex is a crude hesperidin preparation obtained by extraction of the albedo of orange peel with calcium hydroxide solution. On acidification with hydrochloric acid to pH about 4.5, hesperidin precipitates as a crystalline material along with other co-precipitated flavonoids. The precipitate is washed to remove non-flavonoid ballast, and then spray dried. Average hesperidin content is 72%; naringenin-7-rutinoside, 4.4%; isosakuranetin- 7-rutinoside, 4.2%; and less than 1% naringenin-7-rutinoside-4’- glucoside, eriocitrin, sinensetin, bobeletin, tangeretin, and several unidentified polymethoxylated flavones. It contains no rutin. The powdered precipitate is nonhygroscopic; its weight loss on drying is 2-5%; sulfated ash, 2-4%; and methoxyl content, 3.3-3.7%.Purified hesperidin is prepared from hesperidin complex by dissolving the crystals in calcium hydroxide solution and precipitating by acidification with hydrochloric acid. More than one cycle of dissolution and precipitation may be needed to achieve the minimum hesperidin content of 80% specified for the purified product. Most purified product is stated to have a hesperidin content of 90%.Hesperidin is practically tasteless. Presumably through its action as an antioxidant, hesperidin has been reported to delay flavor deterioration of milk-based beverages, thereby extending shelf life by 6-12 months. Hesperidin also is used as a reagent in the refining and reclaiming of lead and zinc, and as a raw material in the production of the dihydrochalcone of neohesperidin, a nonnutritive sweetener.
• Uses: Food additive. Heptyl 4-hydroxybenzoate is a preservative and antimicrobial agent. It is very slightly soluble in water. It may be used in fermented malt beverages to inhibit microbial spoilage and is permitted in beer. It is also termed n-heptyl-para-hydroxybenzoate. n-Heptyl 4-hydroxybenzoate is used for inhibiting microbiological spoilage, used as preservatives, skin care, hair care.

Technology Process of Heptyl 4-hydroxybenzoate

There total 8 articles about Heptyl 4-hydroxybenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.8%

4-Benzyloxy-benzoic acid heptyl ester → heptylparaben (1085-12-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 40 ℃; under 2585.7 Torr;

Reference yield: 67.0%

styrene oxide (96-09-3) + 4-bromo-phenol (106-41-2) + n-heptan1ol (111-70-6) → heptylparaben (1085-12-7) + phenol (108-95-2,27073-41-2)

Guidance literature:

With 5%-palladium/activated carbon; sodium fluoride; In 1,4-dioxane; at 150 ℃; for 6h;

DOI:10.1002/chem.201600570

Reference yield: 42.4%

n-heptan1ol (111-70-6) + 4-hydroxy-benzoic acid (99-96-7) → heptylparaben (1085-12-7)

Guidance literature:

With sulfuric acid; In toluene; for 4h; Heating;

DOI:10.1211/002235702568

upstream raw materials:

n-heptan1ol

4-hydroxy-benzoic acid

4-Methoxycarbonyloxy-benzoic acid heptyl ester

4-(methoxycarbonyloxy)benzoic acid

Downstream raw materials:

C₇₂H₇₂O₁₈

Refernces

• 1、 Zuev. "Dipole architecture of molecules and mesomorphic behavior of liquid crystals with rigid T-shaped mesogenic fragment". experimental part. p. 1559 - 1564. Retrieved 2009/06/28.
• 2、 Owen, Caroline,James, Karen,Sampson, Luther,Ahmed, Sabbir. "Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase". . p. 85 - 93. Retrieved 2007/10/03.