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갈릭산

갈릭산
갈릭산 구조식 이미지
카스 번호:
149-91-7
한글명:
갈릭산
동의어(한글):
갈산;갈릭산;갈릭애씨드
상품명:
Gallic acid
동의어(영문):
gallic;BETZ 0276;gallicaci;GALLIC ACID;AKOS 214-65;Gallussaure;Gallic acid 0;graphite oxide;graphitic acid;kyselinagallova
CBNumber:
CB0158671
분자식:
C7H6O5
포뮬러 무게:
170.12
MOL 파일:
149-91-7.mol

갈릭산 속성

녹는점
251 °C (dec.) (lit.)
끓는 점
259.73°C (rough estimate)
밀도
1.694
굴절률
1.5690 (estimate)
저장 조건
2-8°C
물리적 상태
Powder
산도 계수 (pKa)
4.41(at 25℃)
색상
Off-white
수용성
12 g/L cold water
Merck
14,4345
BRN
2050274
안정성
Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides.
InChIKey
LNTHITQWFMADLM-UHFFFAOYSA-N
CAS 데이터베이스
149-91-7(CAS DataBase Reference)
NIST
Benzoic acid, 3,4,5-trihydroxy-(149-91-7)
EPA
Gallic acid (149-91-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36/37/38
안전지침서 26-36-24/25-37/39
WGK 독일 2
RTECS 번호 LW7525000
F 고인화성물질 8-9-23
TSCA Yes
HS 번호 29182900
유해 물질 데이터 149-91-7(Hazardous Substances Data)
독성 LD50 in rabbits (g/kg): 5.0 orally (Dollahite)
기존화학 물질 KE-34287
그림문자(GHS):
신호 어:
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
NFPA 704
0
2 1

갈릭산 MSDS


3,4,5-Trihydroxybenzoic acid

갈릭산 C화학적 특성, 용도, 생산

개요

Gallic acid is a tri hydroxy benzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5- tri hydroxy benzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins.
Salts and esters of gallic acid are termed 'gallates'. Despite its name, it does not contain gallium.
Gallic acid is commonly used in the pharmaceutical industry. It is used as a standard for determining the phenol content of various analytes by the Folin - Ciocalteau assay; results are reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.
Gallic acid seems to have anti-fungal and anti - viral properties. Gallic acid acts as an antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids contain gallic acid.

개요

Gallic acid is a phenol that has been found in C. sinensis and has diverse biological activities. It scavenges DPPH (Item No. 14805) and hydroxyl radicals in cell-free assays (IC50s = 9.4 and 191 μM, respectively). Gallic acid (1-100 μM) reverses abscisic acid-induced inhibition of hypocotyl growth in A. caudatus seedlings. In vivo, gallic acid (21.8 g/kg) inhibits morpholine- and sodium nitrite-induced adenocarcinoma formation in mice. It also inhibits passive cutaneous anaphylaxis in mice when administered at a dose of 50 mg/kg.

화학적 성질

Colorless crystalline needles or prisms obtained from nutgall tannins,gallic acid is soluble in water and alcohol and melts at 235 to 240 °C. Also known as trihydroxybenzoic acid, it is used in photography, tanning, ink manufacture and pharmaceuticals.

출처

Gallic acid is found in a number of land plants. It is also found in the aquatic plant Myriophyllum spicatum and shows an allelopathic effect on the growth of the blue-green alga Microcystis aeruginosa.
In food
Areca nut
Bearberry (Arctostaphylos sp)
Bergenia sp
Blackberry
Hot chocolate
Juglans regia (Common walnut)
Mango in peels and leaves
Phyllanthus emblica (Indian gooseberry) in fruits
Raspberry
Syzygium aromaticum (clove)
Vinegar
wine
Witch hazel (Hamamelis virginiana)
White tea.

용도

Gallic acid is an important component of iron gall ink, the standard European writing and drawing ink from the 12 th to 19th century with a history extending to the Roman empire and the Dead Sea Scrolls. Pliny the Elder (23-79 AD) describes his experiments with it and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing tannic acid (a macromolecular complex containing gallic acid). It could then be mixed with green vitriol (ferrous sulfate) — obtained by allowing sulfate - saturated water from a spring or mine drainage to evaporate — and gum arabic from acacia trees; this combination of ingredients produced the ink.
Gallic acid was one of the substances used by Angelo Mai (1782–1854), among other early investigators of palimpsests, to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering manuscripts too damaged for subsequent study by other researchers.
Early photographers, including Joseph Bancroft Reade (1801– 1870) and William Fox Talbot (1800 – 1877), used gallic acid for developing latent images in calotypes. It has also been used as a coating agent in zincography.

용도

It can be used to produce polyesters based on phloretic acid and gallic acid.

용도

gallic acid is a potential bleaching agent and anti-oxidant, it is also astringent and potentially anti-microbial and anti-fungal. Scientists are finding that gallic acid may serve as a skin-lightening agent by inhibiting the action of the tyrosinase and peroxidase enzymes. Some studies indicate that it is more effective than hydroquinone when combined with the proper ingredients. It is also incorporated into anti-aging formulations for its ability to prevent mucopolysaccaride deterioration. It is a constituent of witch hazel and oak bark, among many other plants; however, it is generally obtained from nutgalls for commercial purposes.

용도

antineoplastic, astringent, antibacterial

용도

Gallic acid is a trihydroxybenzoic acid found in many plants as either the free acid or in the esterified form of gallotannins and ellagitannins. It demonstrates antioxidant activity by scavenging 2,2-diphenyl-1-picrylhydrazyl and hydroxyl free radicals with IC50 values of 9.4 and 191 μM, respectively, and inhibiting microsomal lipid peroxidation with an IC50 value of 1.51 μM. Gallic acid is often used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay where results are reported in gallic acid equivalents.[Cayman Chemical]

용도

A cyclooxygease inhibitor substance found in plants.

정의

ChEBI: A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.

생명 공학 생산

The production of gallic acid is challenging. Conventionally, it has been produced by acid hydrolysis of tannic acid. However, this process is expensive due to low yields and high impurities. To overcome this problem, microbial production of gallic acid has been suggested. For example, in a solid-state fermentation of Teri pod cover powder containing tannin using Rhizopus oryzae, a yield of 90.9 % based on the tannin content of 58 % of the substrate was observed. In a submerged culture of Aspergillus aceleatus DBF9 growing on a medium with 3 % tannin, a maximal product concentration of 6.8 g.L-1 was reported. With tannic acid, even higher product concentrations of up to 25 g.L-1, a yield of 0.83 g of gallic acid per gram of tannic acid, and a productivity of 0,56 g.L-1.h-1 were shown using Apergillus fischeri MTCC 150 in submerged cultivation. An alternative is the enzymatic hydrolysis of tannic acids using tannase produced by microorganisms (e.g. Aspergillus fischeri or R. oryzae). For example, propyl gallate could be produced using a tannase from Emericela nidulans immobilized on ionic and covalent supports.

일반 설명

Odorless white solid. Sinks in water.

공기와 물의 반응

Sparingly water soluble

반응 프로필

Phenols, such as Gallic acid, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.

건강위험

Inhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation.

화재위험

Flash point data for Gallic acid are not available. Gallic acid is probably combustible.

Biochem/physiol Actions

Gallic acid is a water soluble phenolic acid present in grapes and in the leaves of many plants. Gallic acid esters, such as tannins, catechin gallates and aliphatic gallates are potent antioxidants in vitro. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro.

부작용

It is a weak carbonic anhydrase inhibitor.

신진 대사

Biosynthesis
Chemical structure of 3,5- didehydro shikimate Gallic acid is formed from 3-dehydro shikimate by the action of the enzyme shikimate dehydro genase to produce 3,5-didehydro shikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, where the equilibrium lies essentially entirely toward gallic acid because of the coincidently occurring aromatization.
Degradation
Gallate dioxygenase is an enzyme found in Pseudomonas putida that catalyzes the reaction :
gallate + O2 → (1E)-4-oxobut-1-ene-1,2,4-tri carboxylate.
Gallate decarboxylase is another enzyme in the degradation of gallic acid.
Conjugation
Gallate 1-beta-glucosyltransferase is an enzyme that uses UDPglucose and gallate, whereas its two products are UDP and 1-galloylbeta- D-glucose.

Purification Methods

Crystallise gallic from water. The tri-O-acetyl derivative has m 172o (from MeOH), and the anilide has m 207o(from EtOH). [Beilstein 10 H 470, 10 IV 1993.]

Esters

Also known as galloylated esters:
Methyl gallate
Ethyl gallate, a food additive with E number E313 Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and propanol
Octyl gallate, the ester of octanol and gallic acid
Dodecyl gallate, or lauryl gallate, the ester of dodecanol and gallic acid
Epicatechin gallate, a flavan-3-ol, a type of flavonoid, present in green tea
Epigallocatechin gallate (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin
Gallocatechin gallate (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol
Theaflavin-3-gallate, a theaflavin derivative.

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