CAS 94-62-2|Piperine

Introduction：Basic information about CAS 94-62-2|Piperine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Piperine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles90
8. Synonyms

Common Name	Piperine
CAS Number	94-62-2	Molecular Weight	285.338
Density	1.2±0.1 g/cm3	Boiling Point	498.5±40.0 °C at 760 mmHg
Molecular Formula	C₁₇H₁₉NO₃	Melting Point	131-135 °C(lit.)
MSDS	ChineseUSA	Flash Point	255.3±27.3 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	piperine
Synonym	More Synonyms

Piperine BiologicalActivity

Description	Piperine, a natural alkaloid isolated from Piper nigrum L, inhibits P-glycoprotein and CYP3A4 activities with an IC50 value of 61.94±0.054 μg/mL in HeLa cell.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Membrane Transporter/Ion Channel >>P-glycoproteinNatural Products >>AlkaloidResearch Areas >>Inflammation/Immunology
Target	IC50: 61.94±0.054 μg/mL (P-glycoprotein, HeLa cell)[1]
In Vitro	Piperine has shown to possess in vitro cytotoxic activity and in silico studies. The IC50 value is found to be 61.94±0.054 μg/mL and in silico studies, it has more number of hydrogen bonds with minimum binding and docking energy and may be considered as inhibitor of EGFR tyrosine kinase[1]. Piperine has been found to have immunomodulatory, anti-oxidant, anti-asthmatic, anti-carcinogenic, anti-inflammatory, anti-ulcer, and anti-amoebic properties[2]. Piperine could enhance the bioavailabilities of other drugs including rosuvastatin, peurarin and docetaxel (DOX) via inhibition of CYP3A and P-glycoprotein activity[3].
In Vivo	At the dose of 3.5 mg/kg, the bioavailability of piperine is calculated to be 25.36%. Its AUC0→t is unproportionally increased with doses, indicating a potential non-linear pharmacokinetics profile of piperine. It is found that the AUC0→t and C0 of docetaxel and t1/2of piperine are significantly increased after their combination use, suggesting potential enhanced bioavailability of not only docetaxel but also piperine, which may lead to the overall enhanced pharmacological effects[3]. The phosphorylation of I-κB, p65, p38, ERK, and JNK is inhibited by piperine in a dose-dependent manner, indicating that piperine may be a potential anti-inflammatory drug both in endometritis and in other S. aureus-induced diseases[4].
Cell Assay	Standard solution is prepared by dissolving 10 mg of piperine in 100 mL of methanol. The MTT assay is carried out to measure cell viability. Ten thousand cells in 100 μL of DMEM media are seeded in the wells of a 96-well plate. After 24 h, existing media is removed and 100 μL of various concentrations of piperine (20–100 μg/mL) are added and incubated for 48 h at 37 °C in a CO2 incubator. Control cells are supplemented with 0.05 % DMSO vehicle. At the 48th hour of incubation, MTT (10 μL of 5 mg/mL) is added to the plate. The contents of the plate are pipetted out carefully, the formazan crystals formed are dissolved in 100 μL of DMSO, and the absorbance is measured at 550 nm in a microplate reader[1].
Animal Admin	Rats: The stock solutions of piperine (PIP) and docetaxel (DOX)are prepared by dissolving appropriate amount of each authentic compound in DMSO separately at 1 mg/mL. The standard solutions containing both PIP and DOX are prepared by serial dilution of the stock solutions with 0.2% formic acid and acetonitrile (50:50, v/v) to yield concentrations of 25, 50, 100, 200, 400, 800, 1600, 3200, 6400, 12800 ng/mL. 25 Sprague-Dawley rats are divided into five groups receiving DOX(Group DOX 7 iv, 7 mg/kg, i.v.), PIP (Group PIP 35 po, 35 mg/kg,p.o.) and their combined administration (Group DOX+PIP) as well as PIP (Group PIP 3.5 po, 3.5 mg/kg, p.o.) and PIP (Group PIP 3.5 iv, 3.5 mg/kg, i.v.)[3]. Mice: Piperine is dissolved in 5 mL of tris buffered saline (TBS) at concentrations corresponding to 25, 50, and 100 mg/kg, based on the weight of the mice. After 24 h of S. aureus infection in the uterus, the piperine solution is injected intraperitoneally three times every 6 h. A total of 60 female BALB/c mice are used in this study. All mice are maintained on a 12 h light/dark cycle and cafeteria feeding[4].
References	[1]. Paarakh PM, et al. In vitro cytotoxic and in silico activity of piperine isolated from Piper nigrum fruits Linn. In Silico Pharmacol. 2015 Dec;3(1):9. Epub 2015 Oct 29. [2]. Meghwal M,et al. Piper nigrum and piperine: an update. Phytother Res. 2013 Aug;27(8):1121-30. [3]. Li C, et al. Non-linear pharmacokinetics of piperine and its herb-drug interactions with docetaxel in Sprague-Dawley rats. J Pharm Biomed Anal. 2016 Sep 5;128:286-93. [4]. Zhai WJ, et al. Piperine Plays an Anti-Inflammatory Role in Staphylococcus aureus Endometritis by Inhibiting Activation of NF-κB and MAPK Pathways in Mice. Evid Based Complement Alternat Med. 2016;2016:8597208.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	498.5±40.0 °C at 760 mmHg
Melting Point	131-135 °C(lit.)
Molecular Formula	C₁₇H₁₉NO₃
Molecular Weight	285.338
Flash Point	255.3±27.3 °C
Exact Mass	285.136505
PSA	38.77000
LogP	2.66
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.615
InChIKey	MXXWOMGUGJBKIW-YPCIICBESA-N
SMILES	O=C(C=CC=Cc1ccc2c(c1)OCO2)N1CCCCC1
Stability	Stable. Incompatible with strong oxidizing agents.
Water Solubility	40 mg/L (18 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TN2321500

CHEMICAL NAME :: Piperidine, 1-piperoyl-, (E,E)-

CAS REGISTRY NUMBER :: 94-62-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C17-H19-N-O3

MOLECULAR WEIGHT :: 285.37

WISWESSER LINE NOTATION :: T56 BO DO CHJ G1U2U1V- AT6NTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 514 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15100 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 105 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3500 mg/kg/7D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Kidney, Ureter, Bladder - other changes Related to Chronic Data - death

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: IJSIDW Indian Journal of Pharmaceutical Sciences. (Kalina, Santa Cruz (East), Bombay 400 029, India) V.40(2)- 1978- Volume(issue)/page/year: 40,113,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 15-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 125 mg/kg

SEX/DURATION :: female 8-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 25 mg/kg

SEX/DURATION :: female 8-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn,Xi
Risk Phrases	R21/22
Safety Phrases	S22-S24/25-S36/37
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	TN2321500
HS Code	2939999090

Customs

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles90

Piperine inhibits the growth and motility of triple-negative breast cancer cells.

Cancer Lett. 357(1) , 129-40, (2014)

Piperine, an alkaloid from black pepper, is reported to have anticancer activities. In this study, we investigated the effect of piperine on the growth and motility of triple-negative breast cancer (T...

Piperine from black pepper inhibits activation-induced proliferation and effector function of T lymphocytes.

J. Cell. Biochem. 116 , 2577-88, (2015)

Piperine is a major alkaloid component of black pepper (Piper nigrum Linn), which is a widely consumed spice. Here, we investigated the effect of piperine on mouse T lymphocyte activation. Piperine in...

Development and validation of simultaneous estimation method for curcumin and piperine by RP-UFLC.

Pak. J. Pharm. Sci. 27(4) , 901-6, (2014)

Curcumin and piperine are proven for their potent medicinal benefits to treat various diseases and they are most commonly used combination in various Indian systems of medicine such as Ayurveda, Siddh...

Synonyms

2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-

(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one

5-(1,3-benzodioxol-5-yl)-1-piperidinopenta-2,4-dien-1-one

(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

UNII:U71XL721QK

(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine

1-(5-(3,4-Methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine

trans,trans-1-piperoylpiperidine

FEMA 2909

1-PIPEROYL-(E,E)-PIPERIDINE

Piperine

1-Piperoylpiperidine, (E,E)-

Piperidine, 1-[5- (1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-

piperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-

Piperidine, 1-piperoyl-, (E,E)-

(E,E)-1-piperoylpiperidine

Piperidine, 1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)-

MFCD00005839

PIPERLINE

Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-

Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-

Piperin

1-Piperoylpiperidine

EINECS 202-348-0

Bioperine

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