L-Chicoric Acid ((-)-Chicoric acid) is a dicaffeoyl tartaric acid, a potent, selective and reversible inhibitor of HIV-1 integrase (HIV-1 integrase) with IC50 of about 100 nM. L-Chicoric Acid also inhibits HIV-1 replication in tissue culture.

Physicochemical Properties

Molecular Formula	C22H18O12
Molecular Weight	474.3711
Exact Mass	474.079
CAS #	70831-56-0
Related CAS #	Chicoric acid;6537-80-0
PubChem CID	5281764
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	785.0±60.0 °C at 760 mmHg
Melting Point	206 °C
Flash Point	272.9±26.4 °C
Vapour Pressure	0.0±2.9 mmHg at 25°C
Index of Refraction	1.726
LogP	3.81
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	11
Heavy Atom Count	34
Complexity	740
Defined Atom Stereocenter Count	2
SMILES	C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O
InChi Key	YDDGKXBLOXEEMN-IABMMNSOSA-N
InChi Code	InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
Chemical Name	(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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	At concentrations between 500 nM and 10 μM, L-chocoric acid inhibits integration; however, at values more than 1 μM, it also inhibits entrance. Viral entrance is considerably impacted by L-chichoric acid at doses of 5 μM or above. A decrease in integrated provirus and a rise in the DNA to cDNA ratio of the two LTR circles indicated that L-chichoric acid also impeded integration. About 500 nM is the EC50 of L-chichoric acid against HIV, and this quantity does not prevent HIV from infecting H9 cells [1]. L-chichoric acid had an ED50 of 400 nM against the HIVNL4-3 control virus, but it was completely ineffective against HIVNL4-3 passaged in the presence of 8 μM of this molecule [2].
References	[1]. L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology. 2004 Sep 1;326(2):203-19. [2]. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. J Virol. 1998 Oct;72(10):8420-4. [3]. Robinson WE Jr. L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of a protease inhibitor (AG1350). Antiviral Res. 1998 Aug;39(2):101-11.
Additional Infomation	Chicoric acid is an organooxygen compound. It has a role as a HIV-1 integrase inhibitor and a geroprotector. It is functionally related to a tetracarboxylic acid. Chicoric acid has been reported in Camellia sinensis, Hydrastis canadensis, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~210.81 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.27 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.1081 mL	10.5403 mL	21.0806 mL
	5 mM	0.4216 mL	2.1081 mL	4.2161 mL
	10 mM	0.2108 mL	1.0540 mL	2.1081 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.