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SMB00378

Sigma-Aldrich

Diallyl disulfide

≥98% (HPLC)

Synonym(s):

Allyl disulfide, Diallyl disulfide

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About This Item

Linear Formula:
CH2=CHCH2SSCH2CH=CH2
CAS Number:
2179-57-9
Molecular Weight:
146.27
Beilstein:
1699241
EC Number:
218-548-6
MDL number:
MFCD00008656
UNSPSC Code:
12352200
PubChem Substance ID:
329824979
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

Allium sativum L.

Quality Level

200

vapor density

>5 (vs air)

vapor pressure

1 mmHg ( 20 °C)

Assay

≥98% (HPLC)

form

oil

color

colorless to yellow

refractive index

n20/D 1.541 (lit.)

bp

180-195 °C (lit.)

density

1.008 g/mL at 25 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C=CCSSCC=C

InChI

1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2

InChI key

PFRGXCVKLLPLIP-UHFFFAOYSA-N

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General description

Diallyl disulfide (DADS) is an oil-soluble volatile organosulfur compound that can be naturally found in Allium sativum (garlic).[1][2] It has a simple chemical structure with two sulfur atoms attached with two allyl groups.[2] This constitute of garlic contributes to its pungent aroma.[3]

Application

Diallyl disulfide has been used:
  • to study its effects in apoptosis induction and cell viability on different glioma cell lines[4]
  • as a treatment and positive control to assess the anti-inflammatory regulation of nuclear factor erythroid-2 related factor-2 (Nrf2) in breast cancer cells[5]
  • as a potential substrate compound to detect hydrogen sulfide (H2S) production via lead acetate/lead sulfide method[1]

Biochem/physiol Actions

Diallyl disulfide is a potent anticancer agent.[6] It can reduce carcinogen-induced cancers and shows anti-proliferative effects in both in vivo and in vitro models.[6] DADS enhances the anti-obesity and anti-inflammatory effects of green tea in high-fat/high-sucrose (HF/HS) diet-fed mice.[7] It also displays antioxidant, anti-microbial, cardiovascular protective, and neuroprotective activities.[2] DADS elicits anti-mitotic and anti-neoplastic effects and arrests mitosis in colon neoplastic lesions in vivo and colon tumor cell growth in vitro experiments.[8]
Organosulfur compound that is naturally found in garlic. Contributes to the pungent odor of crushed garlic. Anticancer agent and may provide protection against cardiovascular disease.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000365355
0000350708
0000350708
0000365355
0000244221

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Sigma-Aldrich

W203501

Allyl mercaptan

(+)-L-Alliin analytical standard

Supelco

72805

(+)-L-Alliin

USP

USP

1012950

Alliin

V Robert et al.
Carcinogenesis, 22(8), 1155-1161 (2001-07-27)
Diallyl disulfide (DADS) is a major organosulphur compound present in garlic with an anti-mitotic potential against colon neoplastic lesions in vivo and colon tumour cell growth in vitro. Using the human colon adenocarcinoma HT-29 Glc(-/+) cell line we identified sub-populations
Anna Choromanska et al.
Biomedical reports, 13(4), 32-32 (2020-08-18)
Gliomas are a group of malignant brain tumors. Despite significant efforts to optimize treatment options for patients with high-grade glioma, the prognosis of the overwhelming majority of patients remain poor. This bleak prognosis despite treatment of the glioma, is partly
Jaehoon Bae et al.
The Journal of nutritional biochemistry, 64, 152-161 (2018-12-06)
Obesity is a major problem in developed countries and a burden on social health care systems. Several epidemiological studies showed the protective effects of green tea against obesity-related diseases. Cyclic guanosine monophosphate (cGMP) acts as a mediator for the physiological
Xiuxiu Song et al.
Evidence-based complementary and alternative medicine : eCAM, 2021, 5103626-5103626 (2021-11-09)
Garlic is widely accepted as a functional food and an excellent source of pharmacologically active ingredients. Diallyl disulfide (DADS), a major bioactive component of garlic, has several beneficial biological functions, including anti-inflammatory, antioxidant, antimicrobial, cardiovascular protective, neuroprotective, and anticancer activities.
Effects of drying time on the aroma of garlic (Allium sativum L.) seasoning powder
Li Kaixuan, et al.,
Flavour and Fragrance Journal, 36(1), 99-110 (2021)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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