Diallyl Disulfide (HCID 16590)

概要

Diallyl disulfide is an organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium. It has a role as an antineoplastic agent, an antifungal agent and a plant metabolite.

名称と識別子

優先名称: Diallyl Disulfide
IUPAC: 3-(prop-2-enyldisulfanyl)prop-1-ene
現地名: ジアリルジスルフィド
英語名: Diallyl disulfide
分子式: C6H10S2
分子量: 146.27

名称と別名

DIALLYL DISULFIDE2179-57-9DiallyldisulfideAllyl disulfideDiallyl disulphideDisulfide, di-2-propenylAllyl disulphide2-Propenyl disulphide4,5-Dithia-1,7-octadiene2-Propenyl disulfide3-(prop-2-enyldisulfanyl)prop-1-eneFEMA No. 2028

名称をさらに表示

ジアリルジスルフィドアリル2-プロペニルペルスルフィドジアリルペルスルフィドビス(2-プロペニル)ペルスルフィドジ(2-プロペニル)ペルスルフィドジアリルペルジスルフィド二硫化ジアリルジプロペニルジスルフィドジアリルジスルフィド (TECHNICAL GRADE, >80%)ジアリルジスルフィド, TECH. 80%, REMAINDER MAINLY DIALLYL SULFIDE AND DIALLYL TRISULFIDEアリルジスルフィド / ジアリルジスルフィド二硫化アリルアリルジスルフィドパラトリー3-(プロパ-2-エン-1-イルジスルファニル)プロパ-1-エンヘキサデシル 4-{4-[(ソジオオキシ)スルホニル]フェノキシ}ベンゼン-1-スルホナート(オキシビスベンゼン)-4,4′-ジスルホン酸4-ナトリウム4′-ヘキサデシルDADSFEMA 2028Dially disulfide1,2-diallyldisulfaneDisulfide,di-2-propenylgarlicin oil

DTXSID90352063-(prop-2-en-1-yldisulfanyl)prop-1-ene5HI47O6OA7NSC-29228CHEBI:4488DTXCID7015206NSC29228allyll disulfide

データベース識別子

CAS: 2179-57-9
PubChem CID: 16590
DTXSID: DTXSID9035206
ChEMBL: CHEMBL366603
ChEBI: CHEBI:4488
UNII: 5HI47O6OA7
EC Number: 218-548-6
Nikkaji: J1.800G

物性

構造計算による物性

XLogP: 2.2
極性表面積: 50.6 Å²
水素結合供与体数: 0
水素結合受容体数: 2
回転可能結合数: 5
重原子数: 8
形式電荷: 0
複雑度: 58.9

実験および物理化学的性質

Chemical ClassesOther Classes -> Sulfur Compounds

FragrancesFragrance Ingredient (Allyl disulfide) -> IFRA transparency List

OdorGARLIC ODOR

TasteSHARP, GARLIC FLAVOR

Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density · 2 件

1.010 @ 15 °C

0.998-1.015

物理化学的性質

沸点: 180 · 180-195 °C(lit.)
比重(密度): 1.008 g/mL · 1.008 g/mL at 25 °C(lit.)
蒸気密度: 5 · >5 (vs air)
蒸気圧: 1 mm · 1 mm Hg ( 20 °C)
屈折率: 20 · n20/D 1.541(lit.)
FEMA: 2028 · 2028 | ALLYL DISULFIDE
闪点: 144 °F · 144 °F
貯蔵温度: 2 · 2-8°C
水溶解度: Insoluble in water
溶解性: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
外見: 油
色: 無色～黄色
臭い (Odor): ジアリルジスルフィドは、にんにく油の必須臭気成分です。
臭気閾値(Odor Threshold): 0.00022 ppm · 0.00022ppm
においのタイプ: ニンニクっぽい
由来生物: synthetic
JECFA Number: 572 · 572
BRN: 1699241 · 1699241
Henry's Law Constant: 7.5 · 7.5×10-3 mol/(m3Pa) at 25℃, Mazza (1980)
主な用途: 洗浄剤化粧品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/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
InChIKey: PFRGXCVKLLPLIP-UHFFFAOYSA-N
SMILES: C=CCSSCC=C
LogP: 3.26 · 3.26
CAS データベース: 2179 · 2179-57-9(CAS DataBase Reference)
NISTの化学物質情報: Diallyl disulphide(2179-57-9)
EPAの化学物質情報: Diallyl disulfide (2179-57-9)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H226 (97.4%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1647 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: Disulfide, di-2-propenyl

Regulation (EC) No 1831/2003 (amended)

Diallyl disulfide: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

One of the volatiles in onions responsible for lacrimation; Emergency treatment: Irritants; [HSDB] One of the major allergens in garlic and onions; [Kanerva, p. 1777] Diallyl disulfides (DADs): A moderate eye and strong skin irritant in rabbits; A skin sensitizer in guinea pigs using the Buehler method; Causes breathing abnormalities, wobbly gait, and decreased activity in oral lethal-dose studies of rats; Oral LD50 (rat) = 346 mg/kg; Dermal LD50 (rat) = 1,967 mg/kg; [EPA] Safe when used as a flavoring agent in food; [JECFA] A moderate skin and severe eye irritant; Causes hemolysis in oral lethal-dose study of rats; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]

FDA Requirements121.1164. /FROM TABLE/

Hazard Classes and CategoriesFlam. Liq. 3 (97.4%)

毒性情報

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

Human Toxicity ExcerptsALLYL PROPYL DISULFIDE, ALONG WITH DIALLYL DISULFIDE, IS SAID TO BE ONE OF THE PRINCIPAL VOLATILE SUBSTANCES IN ONION WHICH IRRITATE EYES & CAUSE LACRIMATION.

Non-Human Toxicity ExcerptsDIALYL DISULFIDE HAS AN INHIBITORY EFFECT ON THE HEPATIC MITOCHONDRIAL OXIDATIVE PHOSPHORYLATION IN MICE.

Probable Routes of Human ExposureTHE MAXIMUM CONCN OF VAPOR IN AIR ADVISED FOR INDUSTRIAL CONDITIONS IS 2 TO 3 PPM.

法規制情報

FDA Requirements121.1164. /FROM TABLE/

安全データ

F: 13
wgk: 3
tsca: TSCA listed
rtecs: BB1000000
ridadr: UN 2810 6.1/PG 3
hs_code: 29309090
risk_code: 22-36/37/38-10
化審法: (2)-481
消防法: 危-4-2-III
hazard_code: Xn,Xi
safety_code: 26-36/37/39-37/39-16-36
hazard_class: 6.1
packing_group: II
Hazard Classifications: Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの: 2179-57-9(Hazardous Substances Data)

化学と産業

薬理情報

Metabolism/MetabolitesDiallyl disulfide has known human metabolites that include DADSO and (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[(E)-3-(prop-2-enyldisulfanyl)prop-1-enyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid.

MeSH Pharmacological Classification · 5 件

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Chemical substances that are destructive to spermatozoa used as topically administered vaginal contraceptives.

Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved.

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Cellular LocationsMembrane

用途と製造

Uses · 3 件

Major constituent of garlic oil; [ChemIDplus] Used as synthetic flavoring ingredient; [HSDB] Constitutes 86.9% of diallyl disulfides (DADs) which is 90% active ingredient of biopesticide used to control white rot (fungal pathogen) in onions, garlic, and leeks; DADs are volatile sulfur compounds found in garlic, onions, and other members of Allium species; [EPA]

Farming (Pesticides) [Category: Industry]

SYNTHETIC FLAVORING ADJUVANT OR INGREDIENT

Methods of ManufacturingBY OXIDATION OF ALLYL MERCAPTAN WITH IODINE IN THE PRESENCE OF PYRIDINE & ETHANOL; FROM SODIUM ALLYL THIOSULFATE WITH POTASSIUM HYDROXIDE.

Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 6 件

Disulfide, di-2-propen-1-yl: ACTIVE

IN CONDIMENTS 6.5 PPM; MEATS 7.0 PPM.

GARLIC SYNTHETIC FLAVORING. /FROM TABLE/

SULFUR VOLATILE IN GARLIC; ONION; CHIVES & LEEK; FRESH CABBAGE. /FROM TABLE/

MAIN CONSTITUENT OF ALLIUM SATIVUM ESSENTIAL OIL.

FEMA NUMBER 2028 /FROM TABLE/

応用分野 · 4 件

説明Diallyl disulfide is one of the major allergens in garlic (Allium sativum) and onions. Among patients who are patch-test positive to garlic, all 13 who were tested had positive reactions to diallyl sulfide 5% petrolatum.

天然物の起源Main constituent of Allium sativum essential oil. Reported found in onion (Allium cipa, L.), garlic (Allium sativum L.), chive (Allium schoenoprasum L.), nira (Allium tuberosum rottl.), raw cabbage and caucas (Allium victoralis L.).

使用Diallyldisulfide has a range of uses varying from a Cytocrome P450 inhibitor to vasorelaxant and hypotensive. Being in the class of organosulfur compounds, it carries chemopreventive characteristics .

一般的な説明Allyl disulfide is naturally found in Allium species such as garlic and onion. It is used as a flavoring agent in meat and condiments.

調製方法 · 2 件

製造方法Diallyl disulfide can be prepared by oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol, or from sodium allyl thiosulfate using potassium hydroxide.

純化方法Purify the disulfide by fractional distillation until the molar refractivity is in uniformly good agreement with the calculated value [Small et al. J Am Chem Soc 69 1710 1947]. It has also been purified by gas chromatography [retention times: Carson & Wong J Org Chem 24 175 1959, UV: Koch J Chem Soc 395 1949]. It is present in garlic. [Beilstein 1 IV 2098.]

上流・下流製品情報

上流原料

アリルメルカプタンジアリルセレニドジ(2-プロペニル)ペルテトラスルフィドジアリルペルトリスルフィドアリルスルフィドイソチオシアン酸3-メチルブチルヨウ化アリル

下流製品

エチルメチルペルスルフィド

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

上海将来实业股份有限公司400-0066400 13621662912 · [email protected]

補足説明 · 1 件

定義ChEBI: Diallyl disulfide is an organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium. It has a role as an antineoplastic agent, an antifungal agent and a plant metabolite.

ジアリルジスルフィド

基本情報

概要