Heptylparaben

Last updated
Heptylparaben
Heptyl paraben.svg
Heptyl p-hydroxybenzoate ball-and-stick.png
Names
Preferred IUPAC name
Heptyl 4-hydroxybenzoate
Other names
  • Heptyl p-hydroxybenzoate;
  • Heptyl paraben;
  • Heptylparaben;
  • Nipaheptyl;
  • n-Heptyl 4-hydroxybenzoate;
  • n-Heptyl p-hydroxybenzoate;
  • Heptyl para-hydroxybenzoate;
  • E209
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.832 OOjs UI icon edit-ltr-progressive.svg
E number E209 (preservatives)
PubChem CID
UNII
  • InChI=1S/C14H20O3/c1-2-3-4-5-6-11-17-14(16)12-7-9-13(15)10-8-12/h7-10,15H,2-6,11H2,1H3 Yes check.svgY
    Key: ZTJORNVITHUQJA-UHFFFAOYSA-N Yes check.svgY
  • O=C(OCCCCCCC)c1ccc(O)cc1
Properties
C14H20O3
Molar mass 236.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Heptylparaben (heptyl p-hydroxybenzoate) is a compound with formula C7H15(C6H4OHCOO). It is a paraben which is the heptyl ester of p-hydroxybenzoic acid.

Heptylparaben has also been found to be produced in some microorganisms including Microbulbifer . [1]

As a food additive it has E number E209, and is used as a preservative.

Related Research Articles

Benzoic acid Chemical compound

Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Benzyl alcohol Chemical compound

Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Paraben Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are a class of widely used preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Parabens are effective preservatives in many types of formulas. These compounds, and their salts, are used primarily for their bactericidal and fungicidal properties. They are found in shampoos, commercial moisturizers, shaving gels, personal lubricants, topical/parenteral pharmaceuticals, suntan products, makeup, and toothpaste. They are also used as food preservatives.

Ethylparaben Chemical compound

Ethylparaben (ethyl para-hydroxybenzoate) is the ethyl ester of p-hydroxybenzoic acid. Its formula is HO-C6H4-CO-O-CH2CH3. It is a member of the class of compounds known as parabens.

Methylparaben Chemical compound

Methylparaben, also methyl paraben, one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

Butylparaben Chemical compound

Butylparaben, or butyl p-hydroxybenzoate, is an organic compound with the formula C
4
H
9
O
2
CC
6
H
4
OH
. It is a white solid that is soluble in organic solvents. It has proven to be a highly successful antimicrobial preservative in cosmetics. It is also used in medication suspensions, and as a flavoring additive in food.

Propylparaben Chemical compound

Propylparaben, the n-propyl ester of p-hydroxybenzoic acid, occurs as a natural substance found in many plants and some insects, although it is manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. It is a member of the class of parabens. It is a preservative typically found in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. As a food additive, it has the E number E216.

Polyester Category of polymers, in which the monomers are joined together by ester links.

Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Heptyl acetate (C9H18O2), also known as acetate C-7, is a colorless alcohol-soluble liquid that is the ester formed by the condensation of 1-heptanol and acetic acid.

Sodium phenoxide Chemical compound

Sodium phenoxide (sodium phenolate) is an organic compound with the formula NaOC6H5. It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.

In enzymology, a benzoate 4-monooxygenase (EC 1.14.14.92, Formerly EC 1.14.13.12) is an enzyme that catalyzes the chemical reaction

Chorismate lyase

In enzymology, a chorismate lyase is an enzyme that catalyzes the chemical reaction

LY-341495

LY-341495 is a research drug developed by the pharmaceutical company Eli Lilly, which acts as a potent and selective orthosteric antagonist for the group II metabotropic glutamate receptors (mGluR2/3).

Protocatechuic acid Chemical compound

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.

Alkannin Chemical compound

Alkannin is a natural dye that is obtained from the extracts of plants from the borage family Alkanna tinctoria that are found in the south of France. The dye is used as a food colouring and in cosmetics. It is used as a red-brown food additive in regions such as Australia. Alkannin is deep red in a greasy or oily environment and violet in an alkaline environment.

Ferroverdin refers to three different coordination compounds that were first isolated in 1955 by Chain, Tonolo, and Carilli. It consists of three p-vinylphenyl-3-nitroso-4-hydroxybenzoate ligands complexed with a ferrous ion. Ferroverdin is a green pigment produced in the mycelium of species of Streptomyces. It is claimed to be the “first stable ferrous compound to be found in nature.” There are three types of ferroverdin: A, B, and C. In ferroverdin A, both R groups are hydrogens. In ferroverdin B, R1 is a hydroxyl group (OH) and R2 is a hydrogen (according to a diagram in the paper, the R-groups are on the vinyl group, on the carbon opposite the phenyl; they are respectively trans and cis relative to the phenyl group). In ferroverdin C, R1 is a hydrogen while R2 is a carboxyl group (COOH). Ferroverdin is immune to chelating and oxidizing agents due to the strong interaction between the ligands and ferrous ion. However, it can be broken down by reductive processes.1 The presence of ferroverdin peaks when there are four to eight μg/mL of Fe2+ in the media usually in the form of a salt.

Isopropylparaben Chemical compound

Isopropylparaben is a paraben.

Paroxypropione

Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigonadotropic properties of the drug were discovered in 1951 and it entered clinical use shortly thereafter.

References

  1. Peng, X; Adachi, K; Chen, C; Kasai, H; Kanoh, K; Shizuri, Y; Misawa, N (2006). "Discovery of a Marine Bacterium Producing 4-Hydroxybenzoate and Its Alkyl Esters, Parabens". Applied and Environmental Microbiology. 72 (8): 5556. doi:10.1128/AEM.00494-06. PMC   1538717 . PMID   16885309.