22500-92-1 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 22500-92-1 differently. You can refer to the following data:
1. White or almost white, crystalline powder.
2. Sorbic acid is a tasteless, white to yellow-white crystalline powder
with a faint characteristic odor.
Uses
Pharmaceutic aid (antimicrobial
agent).
Definition
ChEBI: A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.
Production Methods
Naturally occurring sorbic acid may be extracted as the lactone
(parasorbic acid) from the berries of the mountain ash Sorbus
aucuparia L. (Fam. Rosaceae). Synthetically, sorbic acid may be
prepared by the condensation of crotonaldehyde and ketene in the
presence of boron trifluoride; by the condensation of crotonaldehyde
and malonic acid in pyridine solution; or from 1,1,3,5-
tetraalkoxyhexane. Fermentation of sorbaldehyde or sorbitol with
bacteria in a culture medium has also been used.
Pharmaceutical Applications
Sorbic acid is an antimicrobial preservative with antibacterial and
antifungal properties used in pharmaceuticals, foods, enteral
preparations, and cosmetics. Generally, it is used at concentrations
of 0.05–0.2% in oral and topical pharmaceutical formulations,
especially those containing nonionic surfactants. Sorbic acid is also
used with proteins, enzymes, gelatin, and vegetable gums. It has
been shown to be an effective preservative for promethazine
hydrochloride solutions in a concentration of 1 g/L.
Sorbic acid has limited stability and activity against bacteria and
is thus frequently used in combination with other antimicrobial
preservatives or glycols, when synergistic effects appear to occur.
Safety
Sorbic acid is used as an antimicrobial preservative in oral and
topical pharmaceutical formulations and is generally regarded as a
nontoxic material. However, adverse reactions to sorbic acid and
potassium sorbate, including irritant skin reactions and
allergic hypersensitivity skin reactions (which are less frequent),
have been reported.
Other adverse reactions that have been reported include
exfoliative dermatitis due to ointments that contain sorbic
acid, and allergic conjunctivitis caused by contact lens solutions
preserved with sorbic acid.
No adverse reactions have been described after systemic
administration of sorbic acid, and it has been reported that it can
be ingested safely by patients who are allergic to sorbic acid.
However, perioral contact urticaria has been reported.
The WHO has set an estimated total acceptable daily intake for
sorbic acid, calcium sorbate, potassium sorbate, and sodium
sorbate, expressed as sorbic acid, at up to 25 mg/kg bodyweight.
Animal toxicological studies have shown no mammalian
carcinogenicity or teratogenicity for sorbic acid consumed at up
to 10% of the diet.
LD50 (mouse, IP): 2.82 g/kg
LD50 (mouse, oral): 3.20 g/kg
LD50 (mouse, SC): 2.82 g/kg
LD50 (rat, oral): 7.36 g/kg
storage
Sorbic acid is sensitive to oxidation, particularly in the presence of
light; oxidation occurs more readily in aqueous solution than in the
solid form. Sorbic acid may be stabilized by phenolic antioxidants
such as 0.02% propyl gallate.
Sorbic acid is combustible when exposed to heat or flame. When
heated to decomposition, it emits acrid smoke and irritating fumes.
The bulk material should be stored in a well-closed container,
protected from light, at a temperature not exceeding 40℃.
Incompatibilities
Sorbic acid is incompatible with bases, oxidizing agents, and
reducing agents. Some loss of antimicrobial activity occurs in the
presence of nonionic surfactants and plastics. Oxidation is
catalyzed by heavy-metal salts. Sorbic acid will also react with
sulfur-containing amino acids, although this can be prevented by
the addition of ascorbic acid, propyl gallate, or butylhydroxytoluene.
When stored in glass containers, the solution becomes very pH
sensitive; therefore, preparations using sorbic acid as a preservative
should be tested for their microbial purity after prolonged periods
of storage.
Aqueous solutions of sorbic acid without the addition of
antioxidants are rapidly decomposed when stored in polypropylene,
polyvinylchloride, and polyethylene containers.
Regulatory Status
GRAS listed. Accepted as a food additive in Europe. Included in the
FDA Inactive Ingredients Database (ophthalmic solutions; oral
capsules, solutions, syrups, tablets; topical and vaginal preparations).
Included in nonparenteral medicines licensed in the UK.
Included in the Canadian List of Acceptable Non-medicinal
Ingredients.
Check Digit Verification of cas no
The CAS Registry Mumber 22500-92-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,5,0 and 0 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 22500-92:
(7*2)+(6*2)+(5*5)+(4*0)+(3*0)+(2*9)+(1*2)=71
71 % 10 = 1
So 22500-92-1 is a valid CAS Registry Number.
22500-92-1Relevant articles and documents
The Mechanism of Dehydrating Bimodules in trans-Acyltransferase Polyketide Biosynthesis: A Showcase Study on Hepatoprotective Hangtaimycin
Deng, Zixin,Dickschat, Jeroen S.,Dong, Yulu,Lu, Junlei,Luo, Minghe,Qi, Miaomiao,Shen, Kun,Sun, Guo,Sun, Yuhui,Tang, Lingjie,Xiang, Jin,Xu, Houchao,Yin, Zhiyong
supporting information, p. 19139 - 19143 (2021/08/03)
A bioassay-guided fractionation led to the isolation of hangtaimycin (HTM) from Streptomyces spectabilis CCTCC M2017417 and the discovery of its hepatoprotective properties. Structure elucidation by NMR suggested the need for a structural revision. A putative HTM degradation product was also isolated and its structure was confirmed by total synthesis. The biosynthetic gene cluster was identified and resembles a hybrid trans-AT PKS/NRPS biosynthetic machinery whose first PKS enzyme contains an internal dehydrating bimodule, which is usually found split in other trans-AT PKSs. The mechanisms of such dehydrating bimodules have often been proposed, but have never been deeply investigated. Here we present in vivo mutations and in vitro enzymatic experiments that give first and detailed mechanistic insights into catalysis by dehydrating bimodules.
One-flask tethered ring closing metathesis-electrocyclic ring opening for the highly stereoselective synthesis of conjugated Z/E-dienes
Schmidt, Bernd,Kunz, Oliver
, p. 1008 - 1018 (2012/03/27)
A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised. Ring closing metathesis (RCM) of butenoates derived from allylic alcohols can be combined with base-induced ring opening in a one-flask sequence. In this way, dienoic acids become accessible in an operationally simple procedure in very high yields and excellent stereoselectivities, with the tether remaining in the product as a valuable functional group for further transformations. Copyright
Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy
Smith III, Amos B.,Safonov, Igor G.,Corbett, R. Michael
, p. 11102 - 11113 (2007/10/03)
The first total syntheses of (+)-zampanolide (1) and (+)-dactylolide (2), members of a new class of tumor cell growth inhibitory macrolides, have been achieved. Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal. The complete relative and absolute stereochemistries for both (+)-zampanolide and (+)-dactylolide were also assigned, albeit tentatively in the case of (+)-zampanolide (1).
