S-allylmercaptocysteine is an organosulfur compound found in garlic that has anti-inflammatory and antioxidant effects against various lung diseases. S-allylmercaptocysteine exerts anti-cancer effects through multiple pathways, such as inducing apoptosis of cancer cells through the TGF-β signaling pathway, or achieving anti-inflammatory and antioxidant effects by reducing NF-κb activity and up-regulating Nrf2.

Physicochemical Properties

Molecular Formula	C6H11NO2S2
Molecular Weight	193.28704
Exact Mass	193.023
CAS #	2281-22-3
PubChem CID	9794159
Appearance	White to light yellow solid powder
LogP	-2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Heavy Atom Count	11
Complexity	141
Defined Atom Stereocenter Count	1
SMILES	NC(CSSCC=C)C(O)=O
InChi Key	WYQZZUUUOXNSCS-YFKPBYRVSA-N
InChi Code	InChI=1S/C6H11NO2S2/c1-2-3-10-11-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
Chemical Name	(2R)-2-amino-3-(prop-2-enyldisulfanyl)propanoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	S-Allylmercaptocysteine reduces inflammation, oxidative stress, and apoptosis to lessen the nephrotoxicity caused by cisplatin[2]. In SW620, SW480, and Caco-2 cells, S-Allylmercaptocysteine (400 μM; 48 hours) promotes apoptosis, which is measured by looking for activated caspase 3 and cleaved PARP. Cells treated with SAMC have both cleaved PARP1 and activated caspase 3, but untreated control cells do not contain either of these proteins[4].
ln Vivo	In mice with lung fibrosis caused by blast injury (BLM), s-allylmercaptocysteine (25 and 50 mg/kg; oral gavage) could considerably improve the diseased structure and reduce pro-inflammatory cytokines and inflammatory cell infiltration in the bronchoalveolar lavage fluid (BALF). By raising antioxidants such as HO-1, GSH, and SOD and lowering hydroxyproline (HYP) in BLM-induced mice, S-Allylmercaptocysteine has an anti-fibrosis effect[1].
References	[1]. S-allylmercaptocysteine promotes MAPK inhibitor-induced apoptosis by activating the TGF-β signaling pathway in cancer cells. Oncol Rep. 2014;32(3):1124-1132. [2]. S-Allylmercaptocysteine Attenuates Cisplatin-Induced Nephrotoxicity through Suppression of Apoptosis, Oxidative Stress, and Inflammation. Nutrients. 2017;9(2):166. Published 2017 Feb 20. [3]. S-Allylmercaptocysteine attenuates Bleomycin-induced pulmonary fibrosis in mice via suppressing TGF-β1/Smad and oxidative stress pathways. Int Immunopharmacol. 2020;79:106110. [4]. S-allylmercaptocysteine effectively inhibits the proliferation of colorectal cancer cells under in vitro and in vivo conditions. Cancer Lett. 2011;310(1):69-76.
Additional Infomation	See also: S-(Allylthio)-L-cysteine (annotation moved to).

Solubility Data

Solubility (In Vitro)

H2O : 1 mg/mL (5.17 mM) DMSO : < 1 mg/mL

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.1736 mL	25.8679 mL	51.7357 mL
	5 mM	1.0347 mL	5.1736 mL	10.3471 mL
	10 mM	0.5174 mL	2.5868 mL	5.1736 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.