7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

• ChemBase ID: 72946
• Molecular Formular: C30H30O8
• Molecular Mass: 518.5544
• Monoisotopic Mass: 518.19406792
• SMILES: c1(c(c(c(c2c1c(c(c(c2)C)c1c(c2c(cc1C)c(c(c(c2C=O)O)O)C(C)C)O)O)C(C)C)O)O)C=O
• Canonical SMILES: O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C
• InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
• InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
• IUPAC Traditional name: gossypol
• Synonyms: Gossypol; (±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene); (±)-Gossypol from cotton seeds

Database IDs

• CAS Number: 303-45-7
• MDL Number: MFCD00017352
• PubChem SID: 162037866; 24895349
• PubChem CID: 3503
• CHEMBL: 51483
• Chemspider ID: 3383
• KEGG ID: C07667
• Unique Ingredient Identifier: KAV15B369O
• Wikipedia Title: Gossypol

CALCULATED PROPERTIES

• Acid pKa: 7.799882
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 8.017739
• LogD (pH = 7.4): 7.859281
• Log P: 8.019898
• Molar Refractivity: 147.612 cm^3
• Polarizability: 58.13483 Å^3
• Polar Surface Area: 155.52 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Brown solid
• Melting Point: 177–182 °C (decomposes)
• Boiling Point: 707°C
• Density: 1.4 g/mL

Safety Information

• Storage Condition: -20°C; 2-8°C
• RTECS: DU3100000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... AKR1B1(231), BAD(572), BCL2(596), LDHA(3939), LDHB(3945), MCL1(4170)

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02195210

Potential use as male contraceptive by apparently inhibiting LH.

Selleck Chemicals - S2303

Research Area: Cancer
Biological Activity:
Glycyrrhizic acid is a widely used anti-inflammatory agent isolated from the licorice root. It is metabolized to glycyrrhetic acid, which inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the metabolism of corticosteroids. Therefore, glycyrrhizic acid, which is the main and sweet component of licorice, has been investigated for its ability to cause hypermineralocorticoidism with sodium retention and potassium loss, edema, increased blood pressure, as well as depression of the renin-angiotensin-aldosterone system. [1]

Sigma Aldrich - G8761

Biochem/physiol Actions
Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species between two Gossypium species, Gossypium hirsutum and Gossypium barbadens. As a PAF antagonist/inhibitor, Gossypium markedly inhibited the contractile responses of guinea pig lung parenchyma strips stimulated with leukotriene B4, seukotriene D4, and PAF-acether.

REFERENCES

• Poso, H., et al., Lancet , 1 : 885, (1980).
• http://en.wikipedia.org/wiki/Gossypol