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吉草酸

Pentanoic Acid

HCID 7991
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
109-52-4
標準SMILES
CCCCC(=O)O
InChIKey
NQPDZGIKBAWPEJ-UHFFFAOYSA-N
分子式
C5H10O2
平均分子量
102.13 g/mol
単同位体質量
102.06807956

概要

Pentanoic acid appears as a colorless liquid with a penetrating unpleasant odor. Density 0.94 g / cm3. Freezing point -93.2 °F (-34 °C). Boiling point 365.7 °F (185.4 °C). Flash point 192 °F (88.9 °C). Corrosive to metals and tissue.

名称と識別子

優先名称
Pentanoic Acid
IUPAC
pentanoic acid
現地名
吉草酸
英語名
Valeric acid
分子式
C5H10O2
分子量
102.13

名称と別名

Valeric acidPENTANOIC ACID109-52-4n-Valeric acidn-Pentanoic acidValerianic acid1-Butanecarboxylic acidPropylacetic acidButanecarboxylic acidKyselina valerovan-PentanoateValeric acid, normal
名称をさらに表示
吉草酸バレリックアシドN-ペンタン酸N-吉草酸纈草酸ペンタン酸N‐吉草酸N‐吉草酸標準品N-吉草酸標準液 (1ΜG/ΜL水溶液)吉草酸, 99%n-ペンタン酸標準品n-吉草酸標準品valericFEMA 3101Valproic Acid Impurity ANA 1760n-C4H9COOHN-VALERATE
FEMA No. 3101DTXSID7021655GZK92PJM7BNSC-406833DTXCID801655CHEBI:17418RefChem:6342203-677-2

データベース識別子

CAS
109-52-4
PubChem CID
7991
DTXSID
DTXSID7021655
ChEMBL
CHEMBL268736
ChEBI
CHEBI:17418
UNII
GZK92PJM7B
EC Number
203-677-2
Nikkaji
J1.504K

物性

構造計算による物性補完中

XLogP
1.4
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
3
重原子数
7
形式電荷
0
複雑度
59.1

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Organic Acids

Corrosives

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Valeric acid) -> IFRA transparency List
LogP · 4 件

log Kow = 1.39

1.39

1.39

1.39

Odor · 3 件

UNPLEASANT ODOR, SIMILAR TO BUTYRIC ACID

Unpleasant odor

Penetrating odor

Taste · 3 件

Unpleasant flavor, similar to butyric acid

FRUITY TASTE

Penetrating taste

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 5 件

0.939 (USCG, 1999) - Less dense than water; will float

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Danger

H302 (24.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Pentanoic acid

Pentanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanoic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Valeric acid (EC: 203-677-2)

Pentanoic acid: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelCorrosive
Fire Hazards · 2 件

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. (USCG, 1999)

Combustible. Above 86 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible liquid.
Health Hazards · 1 件

Corrosive. Very destructive to tissues of the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, nausea and vomiting. Extremely destructive to skin. May be absorbed through the skin. (USCG, 1999)

化学と産業

薬理情報

Mechanism of Action · 1 件

... Pentanoate was metabolized to a greater extent than octanoate and did not inhibit growth. Pentanoate inhibited acetate utilization in both the inner mitochondrial and peroxisomal compartments as indicated by a reduction in the incorporation of label from [1-14-C]acetate into lipids and into CO2, but there was no difference in oxidation of [2-14-C]pyruvate when pentanoate was the fatty acid substrate as compared to octanoate. Glyconeogenesis was inhibited when pentanoate was substituted for octanoate. ... The effects of 4-pentenoic acid were essentially the same whether octanoate or pentanoate was the fatty acid substrate, i.e. inhibition of glyconeogenesis from all labeled substrates and inhibition of [2-14-C]pyruvate oxidation.

Metabolism/Metabolites · 5 件

It is metabolized by splitting into acetic acid and pyruvic acid.

Labeled valeric acid was incubated with mixed culture of cellulolytic rumen bacteria resulting in the labeling of lipids. The distribution of radioactivity indicated that 1-(14)C-labeled valeric acid was not utilized directly for biosynthesis of higher fatty acids with odd number of carbon atoms by the addition of 2 C, but it was probably degraded into 1-(14)C-labeled acetic acid and into propionic acid.

Valeric acid is formed by rumen microorganisms during the metabolism of proline, leucine, isoleucine, norleucine, and several intermediates of carbohydrate metabolism.

Valeic acid is rapidly metabolized in rat liver to acetate and propionate, giving rise to both glycogen and ketone bodies. This same route of metabolism also predominates in rumen microorganisms.

For more Metabolism/Metabolites (Complete) data for n-PENTANOIC ACID (6 total), please visit the HSDB record page.

Tissue LocationsBladder
Cellular LocationsExtracellular

用途と製造

Uses · 4 件

Used as a sugarcane ripening agent and intermediate; [HSDB] Used in the manufacture of solvents, rodenticides, and fungicides; Present in a variety of plants, fruits, dairy, and meat products; [CHEMINFO]

関連反応

111 件
反応記録を作成
HRID 4989 の反応式
HRID 4989生成物としてuspto-grants-1993_09
HRID 36112 の反応式
HRID 36112反応物としてuspto-grants-1995_05
HRID 42876 の反応式
HRID 42876反応物としてuspto-grants-2013_09
HRID 53061 の反応式
HRID 53061反応物としてuspto-grants-1997_04
HRID 74143 の反応式
HRID 74143生成物として反応物としてuspto-grants-2014_09
HRID 132613 の反応式
HRID 132613反応物としてuspto-grants-2008_06
HRID 134402 の反応式
HRID 134402反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 143085 の反応式
HRID 143085反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
1 / 14 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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0.939 at 20 °C/4 °C

Relative density (water = 1): 0.94

0.935-0.940

0.940 @ 20°C

Flavoring AgentsEU Flavoring substances
Viscosity2.30 cP at 20 °C

物理化学的性質

融点
20 · −20-−18 °C(lit.)
沸点
110 · 110-111 °C10 mm Hg(lit.)
比重(密度)
0.939 g/mL · 0.939 g/mL at 25 °C(lit.)
蒸気密度
3.5 · 3.5 (vs air)
蒸気圧
0.15 mm · 0.15 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.408(lit.)
FEMA
3101 · 3101 | VALERIC ACID
闪点
192 °F · 192 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
40 g/リットル · 40g/リットル
酸解離定数(Pka)
4.84 · 4.84(at 25℃)
外見
液体
色
無色透明~淡黄色
PH
3.95 · 3.95(1 mM solution);3.43(10 mM solution);2.92(100 mM solution);
臭い (Odor)
1 %。気分が悪くなる、腐敗した、酸性、汗ばんだ、悪臭を放つ · プロピレングリコール中1.00%。気分が悪くなる、腐敗した、酸性、汗ばんだ、悪臭を放つ
においのタイプ
俗っぽいです
由来生物
synthetic
臭気閾値(Odor Threshold)
0.000037 ppm · 0.000037ppm
爆発限界(explosive limit)
1.8 · 1.8-7.3%(V)
水溶解度
40 g/L · 40g/L(20℃)
比熱容量
2.06 J/ · Cp(liquid): 2.06 J/(g·K), at 25℃
JECFA Number
90 · 90
Merck
14 · 14,9904
BRN
969454 · 969454
Henry's Law Constant
2.3 · 2.3×101 mol/(m3Pa) at 25℃, Staudinger and Roberts (2001)
Dielectric constant
2.7 · 2.7(20℃)
主な用途
洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア
化粧品成分の機能
香料
InChI
1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)
InChIKey
NQPDZGIKBAWPEJ-UHFFFAOYSA-N
SMILES
CCCCC(O)=O
LogP
1.8 at · 1.8 at 25℃
表面張力
27.23 mN/m · 27.23mN/m at 293.15K
CAS データベース
109 · 109-52-4(CAS DataBase Reference)
NISTの化学物質情報
Pentanoic acid(109-52-4)
EPAの化学物質情報
Valeric acid (109-52-4)
化学的性質 · 3 件

化学的特性ペンタン酸またはバレリック酸としても知られているは化学式C5H10O2を持つ有機化合物ですこの物質は短鎖の飽和脂肪酸の一つであり特有の強い臭いを持つ無色の液体です自然界では植物や微生物によって生成されることがあります

化学的特性Valeric acid has an unpleasant odor and flavor, similar to butyric acid. May consist of one or a mixture of isomers of n-pentanoic acid and/or 2- or 3-methyl-butanoic acid.

化学性质ペンタン酸は水にはあまり溶けませんがエタノールやエーテルといった有機溶剤とは良く溶け合います化学的にはカルボン酸の一種であり他のカルボン酸同様に酸化剤として機能します

Hazards Summary · 1 件

A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; [ICSC] Emergency treatment: Acids; [HSDB] Causes altered sleep time and seizures in intravenous, lethal-dose studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

FDA Requirements · 1 件

Pentanoic acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Reactive GroupAcids, Carboxylic
EC ClassificationSymbol: C; R: 34-52/53; S: (1/2)-26-36-45-61
UN ClassificationUN Hazard Class: 8
Special ReportsLeung HW, Paustenbach DJ; Organic Acids and Bases: Review of Toxicological Studies; Am J Ind Med 18 (6): 717-35 (1990).
Reactivity Profile · 1 件

PENTANOIC ACID is a carboxylic acid. Exothermically neutralizes bases, both organic and inorganic, producing water and a salt. Can react with active metals to form gaseous hydrogen and a metal salt. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts with sulfites, nitrites, thiosulfates and dithionites to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May catalyze (increase the rate of) chemical reactions.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong bases.
Storage ConditionsSeparated from strong bases.
Cleanup MethodsCollect leaking liquid in covered containers. Wash away spilled liquid with plenty of water. Do NOT let this chemical enter the environment.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage DisposalDo NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Wash away remainder with plenty of water.
Preventive MeasuresStrict precautions are necessary in handling ... any skin or eye splashes irrigated with copious amounts of water. /Saturated monocarboxylic acids/
Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear face shield.

毒性情報

Toxicological InformationRanking: 570 (total points: 146.65)
Ecotoxicity Values · 5 件

LC50 Daphnia magna (Water flea) 45 mg/L/48 hr; static /formulated product/

LC50 Lepomis macrochirus (Bluegill) 5,000 mg/L/24 hr /Conditions of bioassay not specified in source examined/ /Na salt/

LC50 Pimephales promelas (Fathead minnow) >100 mg/L/1 hr, static

LC50 Pimephales promelas (Fathead minnow) >100 mg/L/24 hr, static

For more Ecotoxicity Values (Complete) data for n-PENTANOIC ACID (8 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that n-pentanoic acid is expected to have high mobility in soil(SRC). The pKa of n-pentanoic acid is 4.84(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of n-pentanoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.72X10-7 atm-cu m/mole(6). n-Pentanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.96X10-1 mm Hg(7). n-Pentanoic acid is expected to be readily biodegradable in most environmental conditions based on several biodegradation tests where n-pentanoic acid reached 43%(8) to 68%(9) of its theoretical BODs in sewage inoculum after 5 days.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that n-pentanoic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.72X10-7 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). n-Pentanoic acid is expected to be readily biodegradable in most environmental conditions based on several biodegradation tests where n-pentanoic acid reached 43%(7) to 68%(8) of its theoretical BODs in sewage inoculum after 5 days.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-pentanoic acid, which has an estimated vapor pressure of 1.96X10-1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-pentanoic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.9 days(SRC), calculated from its rate constant of 4.11X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Food Survey Values · 1 件

n-Pentanoic acid has been identified as a volatile component of roasted filberts(1), Parma ham(2), fried chicken flavor(3), bacon flavor(4), baked potato flavor(5), and raw beef(6). n-Pentanoic acid was identified as a volatile fatty acid occurring in dalieb fruit pulp at a concn of 5 mg/kg pulp(7). Pentanoic acid has been identified as a volatile flavor component of mutton, chicken, beef, and pork(8). n-Pentanoic acid was identified as a volatile component of microwave popcorn at a concn of 130 ug/kg(9). n-Pentanoic acid was identified as a volatile component of two commercial rice cakes at concns of 210 ppb and 270 ppb(10).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 4 件

Burning sensation. Cough. Sore throat.

Redness. Pain. Skin burns.

Redness. Pain. Severe burns.

Burning sensation. Abdominal pain. Shock or collapse.

Effluent Concentrations · 4 件

n-Pentanoic acid was identified in trench leachate from low-level radioactive waste disposal sites in Maxey Flats, KY and West Valley, NY at an average concn of 3.8 and 47 mg/L, respectively(1). n-Pentanoic acid was detected in raw and processed wastewater from the Lurgi-Process Plant in Sasolburg, South Africa at concns of 12 and 7 mg/L, respectively(2). n-Pentanoic acid was identified as a volatile component of kitchen waste exudate(3). n-Pentanoic acid was identified in the final effluent from the Los Angeles County wastewater treatment plant between Nov 1980 and August 1981 at a concn of 50 ug/L(4). Groundwater samples collected near an area known to be contaminated by wood-preserving chemicals in Pensacola, FL contained n-pentanoic acid at concns of 6.55, 1.53, and 0.51 mg/L 6.1, 3.3, and 5.8 m below the surface, respectively(5). n-Pentanoic acid was detected in groundwater from a landfill well near Norman, OK at an estimated concn of 1.1 ug/L(6). n-Pentanoic acid was detected in the acidic fraction of oil shale retort water at a concn of 210 mg/L(7). Groundwater samples collected 15.5 feet below the land surface near an area contaminated with gasoline contained n-pentanoic acid at a concn of 2 ug/L(8).

n-Pentanoic acid was detected in the leachate of a sanitary landfill located in Barcelona, Spain at an unreported concn(1). n-Pentanoic acid was identified in the effluent of a publicly owned treatment works facility located in an industrial area of NJ at an estimated concn of 8 ppb(2). n-Pentanoic acid was detected in: product water samples from an in situ coal gasification site in Hanna, WY at a concn of 1060 ppm; retort water from in situ oil shale processing in Rock Springs, WY at a concn of 5 ppm; and boiler blowdown water from in situ shale oil processing in DeBeque, CO at a concn of 4 ppm(3). Pentanoic acid was detected in condensate retort water and process retort water from the Occidental Oil Shale, Inc facility in Logan Wash, CO at concns of 0.3 and 110 mg/L, respectively(4). n-Pentanoic acid was identified as a byproduct of chlorine dioxide disinfection of drinking water at a pilot plant in Evansville, IN(5). n-Pentanoic acid was detected in primary and secondary effluents from four sewage treatment plants at concns ranging from 3.7 to 379 ug/L and 0.6 to 40 ug/L, respectively(6).

ONE OF VOLATILE ACIDS IDENTIFIED IN THE RAW SEWAGE IN HAIFA, ISRAEL WAS VALERIC ACID.

n-Pentanoic acid was detected in groundwater down-gradient from a crude oil spill in Bemidiji, MN from 1986-1990 at concentrations ranging from 0.009 to 0.326 uM(1). Samples were taken from distances ranging from 0-90 m downgradient from the spill(1). n-Pentanoic acid was extracted from oil-field wastewater samples from an oil processing facility located in California in concentrations ranging from 0.0009 mg/L to 1.37 mg/L(2).

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

The Koc of n-pentanoic acid is estimated as 140(SRC), using a log Kow of 1.39(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that n-pentanoic acid is expected to have high mobility in soil. In aqueous solution, n-pentanoic acid adsorbed 15.4 and 37.9% onto the clay minerals kaolinite and montmorillonite, respectively, after 144 hours at 22 °C(4). The pKa of n-pentanoic acid is 4.84(5), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6).

TSCA Test Submissions · 5 件

Pentanoic acid (CAS # 109-52-4) was evaluated for subchronic dermal toxicity in New Zealand White rabbits exposed to 0 or 500 mg/kg (in mineral oil solution) non-occluded applications upon abraded skin (3/5 males, 2/5 females) or shaved intact skin (3/5 females, 2/5 males) on 5 consecutive days/week for 2 weeks (10 total applications). One female died on the 7th day of treatment, exhibiting hypopnea, hypoactivity, diminished food consumption, and red anal discharge prior to death. Pharmacotoxic signs noted among survivors included diminished food consumption, nasal discharge, and vocalization upon handling. Without exception, the animals showed transient weight loss in the second week of treatment and worsening signs of dermal irritation including severe erythema, moderate to severe edema, necrosis with eschar, atonia, desquamation, and dermal fissuring. Eschar tissue exfoliated during the second week of treatment and all animals were free of any signs of toxicity by end of study. Upon necropsy, no increased incidence of gross pathological changes relative to controls were identified. Micropathological evaluation of the collective irritative eschar found epidermal hyperplasia, and hyperkeratosis, as well as diffuse and perifollicular dermal inflammation. Rabbits surviving 2-week post-treatment recovery demonstrated some persisting epidermal hyperplasia and hyperkeratosis, but were otherwise free of irritative signs. No significant difference was noted in irritative responses on abraded or intact skin.

n-Pentanoic acid (CAS # 109-52-4) was evaluated for carcinogenic potential in adermal study of C3H/HeJ mice (50/group) administered interscapular applications of 50 mg/kg undiluted test substance twice weekly for 80 weeks. Severe dermal and systemic toxicity noted upon a 4th application was in excess of that observed during an initial pilot study and necessitated amendment of treatment and dermal doses were reduced to 25 mg/kg for the remainder of the study. Despite this change in protocol, decreased survival (10%) among the treated animals relative to controls (no treatment) lowered a final effective number of mice living long enough to develop treatment-related tumors. Depressed bodyweight gains (17%), and epilation, ulceration, and crustiness of the skin at treatment sites were also exhibited among treated mice. The condition of the treated skin further complicated gross recognition of dermal neoplasms. Seven of 12 treated animals demonstrating benign and/or malignant tumors were identified upon microscopic examination of treated dermis, while 5/12 were identified at twice daily examinations during the in-life portion of study. Observed neoplasms in treated mice were characterized as squamous cell carcinomas of the skin (4/4 mice), fibrosarcomas (6/6 mice), fibromas (5/3 mice) and a solitary incidence of keratoacanthoma, relative to one malignant squamous cell carcinoma of the skin noted in a control animal. An average latent period for 5/12 neoplasms observed in living mice was 61.8 weeks. Due to the profound systemic toxicity, 19/50 treated mice also underwent histologic evaluation of all major visceral organs and the brain. No additional gross pathology or microscopic findings in excess of controls was documented.

Natural Pollution Sources · 2 件

THE ACID IS NOT COMMON IN NATURE. REPORTED (AS THE CORRESPONDING ESTER) FOUND IN ESSENTIAL OIL OF BORONIA ANEMONIFOLIA, IN PINEAPPLE FRUITS, & IN OTHER PLANTS; ALSO IDENTIFIED AS ACID OR THE CORRESPONDING ESTER IN THE ESSENTIAL OIL OF LEMON PETITGRAIN.

n-Pentanoic acid was identified as a volatile fatty acid occurring in dalieb fruit pulp at a concentration of 5 mg/kg pulp(1).

法規制情報

FDA Requirements · 1 件

Pentanoic acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

安全データ

F
13
wgk
1
tsca
TSCA listed
rtecs
YV6100000
ridadr
UN 3265 8/PG 3
毒性
LD50 i.v. in mice: 1290 ±53 mg/kg (Or, Wretlind)
hs_code
29156090
risk_code
34-52/53
化審法
(2)-604
消防法
危-4-3-III
hazard_code
C
safety_code
26-36-45-61
hazard_class
8
packing_group
III
自然発火温度
707 °F
Hazard Classifications
Aquatic Chronic 3Eye Dam. 1Skin Corr. 1B
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
109-52-4(Hazardous Substances Data)

Farming (Pesticides) [Category: Industry]

Intermediate for flavors and perfumes, ester-type lubricants, plasticizers, pharmaceuticals, vinyl stabilizers.

As sugarcane ripening agent

U.S. Production · 6 件

2023: 25,000,000 - <40,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1980) 6.81X10+9 grams (est. consumption)

(1981) Probably greater than 2.27X10+6 grams

(1986) >10 million-50 million pounds

For more U.S. Production (Complete) data for n-PENTANOIC ACID (8 total), please visit the HSDB record page.

Consumption PatternsChemical intermediate for polyol esters for lubricants, 87-93%; Chemical intermediate for flavor and fragrance ingredients, 7% (est. 1981)
Industry UsesFuel agents
Methods of Manufacturing · 5 件

Obtained by decompn of n-propylmalonic acid; from n-butyl chloride. Industrial synthesis by oxidation of amyl alcohol or by fermentation processes.

By oxidation of n-amyl alcohol or, together with other isomers, by distillation of valerian roots. Also by reacting butyl bromide and sodium cyanide with subsequent saponification of the formed butyl nitrile.

Reaction of n-butenes with carbon monoxide and hydrogen in presence of cobalt hydrocarbonyl catalyst (oxo process), followed by oxidation of the isolated n-pentanal

Valeraldehyde (carbonyl oxidation)

With other C5 acids by distillation from valerian, by oxidation of n-amyl alcohol, numerous essential oils.

Formulations/PreparationsGrades: Technical; reagent.
Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 4 件

All Other Basic Organic Chemical Manufacturing

Pentanoic acid: ACTIVE

Volatile oil of Bupleurum chinense was separated into 5 fractions. One of the antiinflammatory constituents was identified as valeric acid.

FEMA number: 3101. Non-alcoholic beverages 11.09 ppm; Candy 25.18 ppm; Baked goods 33.51 ppm.

応用分野 · 8 件

解説n-吉草酸(valerianic acid,pentanoic acid):CH3CH2CH2CH2COOH.不快臭のある液体.融点-34.5 ℃,沸点186~187 ℃,97 ℃(2.9 kPa).d2040.9387.n2041.4086.30倍の水に可溶,エタノール,エーテルに易溶.香料の合成原料.飽和鎖式カルボン酸の一つ。ペンタン酸ともいう。 バレロニトリルの加水分解、またはn-アミルアルコール(1-ペンタノール)の酸化により調製される。不快なにおいをもつ無色の液体で、エタノール(エチルアルコール)やエーテルにはよく溶けるが、水にはわずかしか溶けない。酸としての性質を示し、水酸化アルカリや炭酸アルカリの水溶液には塩を生成して溶ける。また、アルコールと反応してエステルを生成する。生薬(しょうやく)の吉草根(きっそうこん)に含まれているのは、主として異性体のイソ吉草酸(CH3)2CHCH2COOHである。

用途着香料、有機合成原料。

用途大気中n-吉草酸のGC分析用標準液。

説明Valeric acid, or pentanoic acid, is a straight - chain alkyl carboxylic acid with the chemical formula C5H10O2. Like other lowmolecular- weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors. Valeric acid appears similar in structure to GHB and the neurotransmitter GABA in that it is a short-chain carboxylic acid, although it lacks the alcohol and amine functional groups that contribute to the biological activities of GHB and GABA, respectively. It differs from valproic acid simply by lacking a 3- carbon side - chain.

天然物の起源The acid is not too common in nature; reported (as the corresponding ester) found in the essential oil of Boronia anemonifolia, in pineapple fruits and in other plants; also identified as acid or the corresponding ester in the essential oil of lemon petitgrain. Also reported found in apple, apple juice, banana, orange juice, bilberry, cranberry, strawberry, raspberry, papaya, grapes, celery, onion, baked potato, tomato, corn mint oil, breads, cheeses, milk, yogurt, butter, cheddar cheese, lean and fatty fish, fish oil, cooked meats, hop oil, beer, rum, whiskies, grape wines, cocoa, tea, roasted filberts, peanuts and pecans, honey, soybeans, coconut meat and milk, cloudberry, passion fruit, starfruit, trassi, mango, jackfruit, licorice, calamus, sake, buckwheat, watercress, laurel, peated malt, wort, kiwifruit, loquat, Bourbon vanilla, shrimps, oyster, scallop, cape gooseberry, sea buckthorn, Chinese quince and maté.

使用valeric acid is obtained from valerian extract, which is considered skin conditioning.

一般的な説明A colorless liquid with a penetrating unpleasant odor. Density 0.94 g / cm3. Freezing point -93.2°F (-34°C). Boiling point 365.7°F (185.4°C). Flash point 192°F (88.9°F). Corrosive to metals and tissue.

使用用途吉草酸は、食品用のフレーバーに広く用いられています。その際には、吉草酸ブチルや吉草酸ペンチルなどのエステルが使用されます。 吉草酸の香りは不快と言われていますが、少量であれば果実の香りを有する場合が多く、果実のエッセンスや精油の成分として利用可能です。リンゴ、モモ、アプリコットなどのフルーツ系、バター、ナッツ系の香料として利用されており、4.2~15ppm程度の濃度です。チューインガムには、260ppmほどの濃度で用いられます。

調製方法 · 2 件

製造方法By oxidation of n-amyl alcohol or, together with other isomers, by distillation of valerian roots; also by reacting butyl bromide and sodium cyanide with subsequent saponification of the formed butyl nitrile.

純化方法Water is removed from the acid by distillation using a Vigreux column (p 11), until the boiling point reaches 183o. A few crystals of KMnO4 are added, and after refluxing, the distillation is continued. [Andrews & Keefer J Am Chem Soc 83 3708 1961, Beilstein 2 H 299, 2 I 130, 2 II 263, 2 III 663, 2 IV 868.]

上流・下流製品情報

上流原料

ブチロニトリル1-ブロモブタン1-ペンタノール

下流製品

バレロニトリルバニリン酸酢酸3-クロロ-4-オキソペンチル2-ブロモ吉草酸シクロヘキサンペンタン酸アリル1-ペンタノール吉草酸ブチル吉草酸エチルバレルアルデヒドバレリルクロリドノナフルオロ吉草酸ε-カプロラクタム2-メチル-2-ヘキサノール吉草酸イソアミル吉草酸フェニル吉草酸ペンチルペンタン酸-2,2-D2

補足説明

定義ChEBI: A straight-chain saturated fatty acid containing five carbon atoms.

n-Valeric acid (CAS # 109-52-4) was evaluated for genotoxic effects in the Chinese Hamster Ovary (CHO)/HGPRT gene mutation test. Based on preliminary cytotoxicity tests, cultures of chinese hamster ovary cells incorporating metabolic activation with Aroclor 1254-induced S-9 rat liver homogenate were exposed for 5 hours to concentrations of 0.2 to 1.6 mg/ml, while non-activated cultures were exposed to concentrations of 0.6 to 1.4 mg/ml. In both activated and non-activated cultures, doses of 1.0 mg/ml and above were associated with excessive cytotoxicity, however throughout the range of exposure concentrations no dose-related mutagenicity was established relative to solvent control (ethanol). Investigators reported a steep cytotoxicity curve for the test substance and CHO cells at 1.0 - 1.3 mg/ml. A numerical increase in mutagenicity was seen in association with 0.6 mg/ml exposures in the non-activated cultures, and background mutagenicity in control cultures with metabolic activation were found excessively high relative to historical controls. These findings prompted a second investigation of test concentrations centered about 0.6 mg/ml in metabolically non-activated cultures. In the CHL/HGPRT gene mutation test with concentrations of 0.20 to 0.60 mg/ml (-S9) and 0.60 to 1.20 (+S9), no reproducible or dose-related mutagenic effects were noted in association with any concentration in either culture preparation.

n-Valeric acid (CAS # 109-52-4) was evaluated for genotoxic effects in the Chinese Hamster Ovary (CHO)/HGPRT in vitro chromosome aberration test. Based on preliminary cytotoxicity tests and equivocal results in an initial genotoxicity test, ovary cell cultures incorporating metabolic activation with Aroclor 1254-induced S-9 rat liver homogenate were exposed for 8 or 12 hours to concentrations of 0.6 to 1.2 mg/ml, while non-activated cultures were exposed to concentrations of 0.07 to 0.2 mg/ml. Cytotoxicity testing established that, in activated and non-activated cultures, 1.2 and 0.3 mg/ml were associated with 66.7% and 55.6% reduction in the respective mitotic indices. In genotoxicity testing, incidence of chromosome aberrations were determined from 100-cell samples of those cultures exposed to the highest concentrations not producing excessive mitotic inhibition. S9-activated cultures exposed to 1.1 and 1.2 mg/ml sampled at both 8 hours and 12 hours demonstrated significant (p < 0.05 and 0.01, respectively) dose-related clastogenic effects relative to control (ethanol solvent), as did the 0.2 mg/ml exposed non-activated cultures (p < 0.05) sampled at 12 hours. Chromatid breaks characterized the majority of aberrations associated with the test substance.

Valeric acid (C-180; 109-52-4) was evaluated for developmental effects in 22 female Crl:COBS, CD(SD)BR rats administered 750 mg/kg of the test substance by gavage on days 6 through 15 of gestation. A control group received corn oil. Maternal animals showed an increased incidence of clinical observations (specific signs not reported). Offspring showed an increased incidence of delayed ossification of several bone structures.