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Primin

Primin is a naturally occurring compound found in the leaf and stem trichomes of Primula obconica and has antibacterial and anticancer properties.
Primin
Primin Chemical Structure CAS No.: 15121-94-5
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
1g
Other Sizes
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Product Description
Primin is a naturally occurring compound found in the leaf and stem trichomes of Primula obconica and has antibacterial and anticancer properties.
Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone) is a naturally occurring benzoquinone first identified in primrose leaves (Primula obconica) and also found in Miconia species. It has shown significant antimicrobial and antitumour properties. Primin was marketed for several years by LAFEPE (Pharmaceutical Laboratory of Pernambuco State, Brazil), but later removed from the market due to its contact sensitising effects and low commercial demand. [2]
Biological Activity I Assay Protocols (From Reference)
Animal Protocol
Toxicity test (acute toxicity): Adult male Swiss white mice (approx. 25-28 g) were fasted for 20 hours before injection. Primin was diluted in Tween 80 (two drops) and saline (0.9%). A single intraperitoneal injection was given, and general effects were observed for 60 minutes and continued for about 72 hours after injection. The control group received solvent only. Doses tested for Primin were 14 mg/kg, 10 mg/kg, and 9 mg/kg. [2]
Antitumour activity test: Female mice (approx. 20-25 g) were divided into groups. Transplants of tumour fragments (about 1.5-2 mm) of sarcoma S-180 and Ehrlich carcinoma were made subcutaneously in the lateral thoracic wall of 6 mice. Starting 48 hours later, injections of test compounds were administered intraperitoneally once daily for 8 days. After treatment, tumours were removed and measured. The efficacy of treatment was estimated by the ellipsoid formula, and the volume of the control group was taken as 100%. [2]
Toxicity/Toxicokinetics
In acute toxicity tests in mice, Primin caused deaths at the following doses: 14 mg/kg (3 out of 6 mice died), 10 mg/kg (2 out of 6 mice died), and 9 mg/kg (1 out of 6 mice died). The LD50 of Primin was determined to be 14 mg/kg. Observed behavioural effects included lethal hydric retention, labored breathing, and decreased muscle tone in some animals. [2]
References

[1]. Biosynthesis of primin and miconidin and its derivatives. Phytochemistry, 1996;41(2), 451–456.

[2]. Synthesis and antitumour activity of the Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone) and analogues. Med Chem. 2007 Jul;3(4):369-72.

Additional Infomation
Primin is a 1,4-benzoquinone compound with a methoxy substituent at position 2 and an pentyl substituent at position 6. It possesses multiple functions, including hapten, metabolite, antibacterial agent, antifeedant, and allergen. Primin has been reported to be found in Cophinforma mamane, Primula halleri, and other organisms with relevant data. See also: Flower (part) of Primula veris.
Primin is known for its allergenic properties and as a strong sensitiser that induces contact dermatitis. The hydroquinone form of Primin, miconidin (2), was about three times less active than Primin in antitumour assays against sarcoma 180 and Ehrlich carcinoma. The quinone group is considered important for cytotoxic activity via formation of semiquinone radical anion. [2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H16O3
Exact Mass
208.109
CAS #
15121-94-5
PubChem CID
84800
Appearance
Light yellow to yellow solid
Density
1.1±0.1 g/cm3
Boiling Point
316.9±31.0 °C at 760 mmHg
Melting Point
77-79 °C
Flash Point
137.7±24.9 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.496
Source
Originated from plants: other families
LogP
2.99
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Heavy Atom Count
15
Complexity
324
Defined Atom Stereocenter Count
0
SMILES
O(C([H])([H])[H])C1=C([H])C(C([H])=C(C1=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
InChi Key
WLWIMKWZMGJRBS-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H16O3/c1-3-4-5-6-9-7-10(13)8-11(15-2)12(9)14/h7-8H,3-6H2,1-2H3
Chemical Name
2-methoxy-6-pentylcyclohexa-2,5-diene-1,4-dione
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: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~480.2 mM; with ultrasonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
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Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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