Cat. No.: HY-15464D

(S)-Gossypol (acetic acid)

(Synonyms: (S)-(+)-Gossypol acetic acid)

5 Cited Publications

Customer Review

Based on 5 publication(s) in Google Scholar

(S)-Gossypol is the isomer of a natural product Gossypol. (S)-Gossypol binds to the BH3-binding groove of Bcl-xL and Bcl-2 proteins with high affinity.

For research use only. We do not sell to patients.

Purity: 98.46%
CAS No.: 1189561-66-7
Formula: C₃₂H₃₄O₁₀
Molecular Weight:578.61

Storage:

-20°C, protect from light, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

(S)-Gossypol (acetic acid) Chemical Structure

CAS No.: 1189561-66-7

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Publications (5)
Solvent & Solubility
- In Vitro
- In Vivo
Protocol
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

(S)-Gossypol is the isomer of a natural product Gossypol. (S)-Gossypol binds to the BH3-binding groove of Bcl-xL and Bcl-2 proteins with high affinity.

IC₅₀ & Target^[1]

Bcl-2

Bcl-xL

All Bcl-2 Family Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
B16-F10	IC₅₀	5.56 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against mouse B16/F10 cells after 48 hrs by MTT assay Antiproliferative activity against mouse B16/F10 cells after 48 hrs by MTT assay	[PMID: 22739087]
Cancer cell lines	GI₅₀	2.85 μM Compound: (+/-)-Gossypol	Cytotoxicity against human non-small cell lung cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human non-small cell lung cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	2.97 μM Compound: (+/-)-Gossypol	Cytotoxicity against human CNS cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human CNS cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.16 μM Compound: (+/-)-Gossypol	Cytotoxicity against human renal cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human renal cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.19 μM Compound: (+/-)-Gossypol	Cytotoxicity against human colon cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human colon cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.5 μM Compound: (+/-)-Gossypol	Cytotoxicity against human ovarian cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human ovarian cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
HEK293	IC₅₀	11.04 μM Compound: AT-101	Cytotoxicity against human HEK293 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human HEK293 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 27353532]
HeLa	IC₅₀	0.08 μg/mL Compound: 18	Cytotoxicity against human HeLa cells by SRB assay Cytotoxicity against human HeLa cells by SRB assay	[PMID: 18553924]
HepG2	IC₅₀	10.16 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay	[PMID: 22739087]
HL-60	IC₅₀	6.6 μM Compound: AT-101	Cytotoxicity against human HL60 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human HL60 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 27353532]
HT-29	IC₅₀	>5 μg/mL Compound: 18	Cytotoxicity against human HT29 cells by SRB assay Cytotoxicity against human HT29 cells by SRB assay	[PMID: 18553924]
K562	IC₅₀	4.55 μM Compound: (R)-Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 25818766]
K562	IC₅₀	7.31 μM Compound: Gossypol	Antiproliferative activity against human K562 cells by MTT assay Antiproliferative activity against human K562 cells by MTT assay	[PMID: 26421995]
K562	IC₅₀	5.91 μM Compound: Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 26620718]
K562	IC₅₀	5.6 μM Compound: Gossypol	Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
K562	IC₅₀	8.28 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 28233676]
KB	IC₅₀	0.04 μg/mL Compound: 18	Cytotoxicity against human KB cells by SRB assay Cytotoxicity against human KB cells by SRB assay	[PMID: 18553924]
Leukemia cell	GI₅₀	2.47 μM Compound: (+/-)-Gossypol	Cytotoxicity against human leukemia cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human leukemia cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
MDA-MB-231	IC₅₀	1.9 μM Compound: 1	Growth inhibition of human MDA-MB-231 cells after 4 days by WST-based assay Growth inhibition of human MDA-MB-231 cells after 4 days by WST-based assay	[PMID: 17552510]
MDA-MB-231	IC₅₀	3.7 μM Compound: 2, R-(-)-gossypol	Growth inhibition of human MDA-MB-231 2LMP cells after 4 days by WST-8 based assay Growth inhibition of human MDA-MB-231 2LMP cells after 4 days by WST-8 based assay	[PMID: 18237106]
MDA-MB-231	IC₅₀	9.21 μM Compound: (R)-Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 25818766]
MDA-MB-231	IC₅₀	4.8 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells by MTT assay Antiproliferative activity against human MDA-MB-231 cells by MTT assay	[PMID: 26421995]
MDA-MB-231	IC₅₀	9.42 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 26620718]
MDA-MB-231	IC₅₀	9.23 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
MDA-MB-231	IC₅₀	8.54 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 28233676]
MDCK	CC₅₀	3.53 μM Compound: Gossypol	Cytotoxicity against MDCK cells by MTT assay Cytotoxicity against MDCK cells by MTT assay	[PMID: 22226654]
Melanoma cell	GI₅₀	3.22 μM Compound: (+/-)-Gossypol	Cytotoxicity against human melanoma cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human melanoma cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
NCI-H1299	EC₅₀	6 μM Compound: 1, Gossypol	Cytotoxicity against human H1299 cells assessed as cell viability after 72 hrs by ATP-LITE assay Cytotoxicity against human H1299 cells assessed as cell viability after 72 hrs by ATP-LITE assay	[PMID: 19555126]
NCI-H460	EC₅₀	3 μM Compound: 1, Gossypol	Cytotoxicity against human H460 cells assessed as cell viability after 72 hrs by ATP-LITE assay Cytotoxicity against human H460 cells assessed as cell viability after 72 hrs by ATP-LITE assay	[PMID: 19555126]
PC-3	IC₅₀	2.5 μM Compound: 2, R-(-)-gossypol	Growth inhibition of human PC3 cells after 4 days by WST-8 based assay Growth inhibition of human PC3 cells after 4 days by WST-8 based assay	[PMID: 18237106]
PC-3	IC₅₀	6.71 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 22739087]
PC-3	IC₅₀	6.26 μM Compound: (R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 25818766]
PC-3	IC₅₀	5.61 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells by MTT assay Antiproliferative activity against human PC3 cells by MTT assay	[PMID: 26421995]
PC-3	IC₅₀	5.78 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 26620718]
PC-3	IC₅₀	7.54 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells measured after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
PC-3	IC₅₀	8.58 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 28233676]
TZM	CC₅₀	9.76 μM Compound: Gossypol	Cytotoxicity in human TZM-bl cells by MTT assay Cytotoxicity in human TZM-bl cells by MTT assay	[PMID: 22226654]

In Vitro

The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (S)-Gossypol ((+)-Gossypol) enantiomers. (+)-Gossypol and (-)-Gossypol binds to Bcl-2 or Bcl-xL with similar binding affinities. (-)-Gossypol is more potent than (+)-Gossypol in inhibition of cell growth and induction of apoptosis. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. (-)-Gossypol exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001)^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS No. 1189561-66-7
Appearance Solid
Molecular Weight 578.61
Formula C₃₂H₃₄O₁₀
Color Light yellow to yellow
SMILES

OC1=C2C(C=O)=C(O)C(O)=C(C(C)C)C2=CC(C)=[C@@]1[C@@]3=C(C)C=C4C(C(C)C)=C(O)C(O)=C(C=O)C4=C3O.CC(O)=O
Synonyms

(S)-(+)-Gossypol acetic acid
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

-20°C, protect from light, stored under nitrogen

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

Publications (5)

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Microb Pathog

Natural small molecule compounds targeting Wnt signaling pathway inhibit HPV infection. [Abstract]

2024 Nov:196:106960. PMID: 39313132
Food Chem Toxicol

Melatonin protects porcine oocytes from gossypol-induced meiosis defects via regulation of SIRT1-mediated mitophagy. [Abstract]

2025 Jan:195:115122. PMID: 39571718

(S)-Gossypol (acetic acid) purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]

Representative images of cumulus expansion in Gossypol (0, 10, 20, 40 μM) -exposed oocytes after 44 h culture in vitro maturation.

(S)-Gossypol (acetic acid) purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]

(A) Illustrative images of ROS staining of Gossypol (0, 10, 20, 40 μM)-exposed oocytes. (B) Fluorescence intensity of ROS in control and gossypol treatment groups.

(S)-Gossypol (acetic acid) purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]

Expression of oxidative stress-related genes (CAT, GSH-Px, SOD1, and SOD2) in control and Gossypol (0, 10, 20, 40 μM) treatment groups in porcine oocytes.

(S)-Gossypol (acetic acid) purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]

Illustrative images of mitochondrial membrane potential (MMP) in Gossypol (0, 10, 20, 40 μM) -exposed oocytes.

(S)-Gossypol (acetic acid) purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]

Expression of PINK1/Parkin-mediated mitophagy related proteins (PINK1, Parkin and P62) of Gossypol (20 μM)-exposed oocytes treated with melatonin. Statistical analysis of the expressions of PINK1/Parkin-mediated mitophagy related proteins in control, gossypol treatment and gossypol-melatonin co-treatment groups.
Transbound Emerg Dis

Gossypol Affects Viral Replication by Inhibiting Pseudorabies Virus Adsorption. [Abstract]

2023 Nov 11:2023:9073566. PMID: 40303819
Anticancer Res

Gossypol Inhibits GLI3-dependent SHH Signaling to Selectively Target SPOP-deficient Breast Cancer Cells. [Abstract]

2026 May;46(5):2317-2327. PMID: 42049345
Patent

US20220162561A1.

Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL (86.41 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

1.7283 mL

8.6414 mL

17.2828 mL

5 mM

0.3457 mL

1.7283 mL

3.4566 mL

10 mM

0.1728 mL

0.8641 mL

1.7283 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Dilution Calculator

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (4.32 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Protocol

Cell Assay

Two representative UM-SCC cell lines, UM-SCC-6 and UM-SCC-14A, are continuously exposed to 0 (vehicle control), 5 or 10 μM (±)-Gossypol, (-)-Gossypol or (S)-Gossypol ((+)-Gossypol) in a 6-day MTT cell survival assay^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (280 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	1.7283 mL	8.6414 mL	17.2828 mL	43.2070 mL
	5 mM	0.3457 mL	1.7283 mL	3.4566 mL	8.6414 mL
	10 mM	0.1728 mL	0.8641 mL	1.7283 mL	4.3207 mL
	15 mM	0.1152 mL	0.5761 mL	1.1522 mL	2.8805 mL
	20 mM	0.0864 mL	0.4321 mL	0.8641 mL	2.1603 mL
	25 mM	0.0691 mL	0.3457 mL	0.6913 mL	1.7283 mL
	30 mM	0.0576 mL	0.2880 mL	0.5761 mL	1.4402 mL
	40 mM	0.0432 mL	0.2160 mL	0.4321 mL	1.0802 mL
	50 mM	0.0346 mL	0.1728 mL	0.3457 mL	0.8641 mL
	60 mM	0.0288 mL	0.1440 mL	0.2880 mL	0.7201 mL
	80 mM	0.0216 mL	0.1080 mL	0.2160 mL	0.5401 mL

Keywords

(S)-Gossypol (acetic acid)

5 Cited Publications

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(S)-Gossypol (acetic acid)

Drug Repurposing Compound Library Plus

Clinical Compound Library Plus

Publications Citing Use of MedChemExpress (MCE) (S)-Gossypol (acetic acid)

All Bcl-2 Family Isoforms

Biological Activity

Chemical Information

Publications (5)

Solvent & Solubility

Protocol

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

(S)-Gossypol (acetic acid)

Drug Repurposing Compound Library Plus

Clinical Compound Library Plus

Publications Citing Use of MedChemExpress (MCE) (S)-Gossypol (acetic acid)

All Bcl-2 Family Isoforms

Biological Activity

Chemical Information

Publications (5)

Solvent & Solubility

Protocol

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

(S)-Gossypol (acetic acid) Related Classifications

HY-15464D Related Classifications