12-O-tetradecanoylphorbol-13-acetate

Modify Date: 2024-01-08 10:22:34

12-O-tetradecanoylphorbol-13-acetate structure	Common Name	12-O-tetradecanoylphorbol-13-acetate
	CAS Number	16561-29-8	Molecular Weight	616.825
	Density	1.2±0.1 g/cm3	Boiling Point	698.1±55.0 °C at 760 mmHg
	Molecular Formula	C₃₆H₅₆O₈	Melting Point	N/A
	MSDS	Chinese USA	Flash Point	208.1±25.0 °C

Use of 12-O-tetradecanoylphorbol-13-acetate

Phorbol 12-myristate 13-acetate (PMA), a phorbol ester, is a commonly used PKC activator.

Name	phorbol 13-acetate 12-myristate
Synonym	More Synonyms

Description	Phorbol 12-myristate 13-acetate (PMA), a phorbol ester, is a commonly used PKC activator.
Related Catalog	Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Research Areas >> Inflammation/Immunology Natural Products >> Others
Target	PKC:11.7 nM (EC50)
In Vitro	In order to examine the role of PKC in p38MAPK phosphorylation, the cells are stimulated with the PKC activator, PMA (100 nM), which mimics the binding of DAG, the natural activator of PKC, to the C1 region of the PKCs. p38MAPK phosphorylation by PMA is observed in the two cell types similar to that observed by GnRH in αT3-1 cells, that is, a slow sustained activation (3.2-fold and 3.6-fold, respectively at 30 min). The paradoxical findings that PKCs activated by GnRH and PMA play a differential role in p38MAPK phosphorylation may be explained by differential localization of the PKCs. Basal, GnRH- and PMA- stimulation of p38MAPK phosphorylation in αT3-1 cells is mediated by Ca2+ influx via voltage-gated Ca2+ channels and Ca2+ mobilization, while in the differentiated LβT2 gonadotrope cells it is mediated only by Ca2+ mobilization[2].
In Vivo	PMA is a PKC agonist, which reverses the damage induced by 5-hydroxydecanoic acid (5-HD). Thus, activation of the mitoKATP protected mitochondrial function in SOD and MDA via the PKC pathway[3].
Cell Assay	αT3-1 and LβT-2 cells are grown in monolayer cultured in DMEM supplemented with 10% fetal calf serum (FCS) and L-glutamine 2 mM, penicillin and streptomycin (100 units/mL) in humidified incubator 5% CO2 at 37°C. Serum starvation is with 0.1% FCS in the same medium for 16 h. GnRH and PMA are then added for the length of time as indicated. In general, αT3-1 cells are transiently transfected by ExGen 500 or by jetPRIME, while LβT2 cells only by jetPRIME transfection reagent. For experiments with dominant-negative (DN) PKCs, αT3-1 cells (in 6 cm plates) are transfected with 1.5 μg of p38α-GFP with 3 μg of control vector, pCDNA3, or with 3 μg of the DN-PKCs constructs. For LβT2 cells, transfections are performed (in 10 cm plates) with 4 μg of p38α-GFP along with 9 μg of control vector, pCDNA3, or with 9 μg of the DN-PKCs constructs. Approximately 30 h after transfection, the cells are serum starved (0.1% FCS) for 16 h and later stimulated with GnRH or PMA, washed twice with ice-cold PBS, treated with the lysis buffer, followed by one freeze-thaw cycle. Cells are harvested; following centrifugation (15,000×g, 15 min, 4°C) supernatants are taken for immunoprecipitation experiments[2].
Animal Admin	Rats[3] All experiments qre performed with male Wistar rats (weighing 250-280 g). One hundred and thirty-five Wistar rats are randomly divided into seven groups. (1) Rats in the sham group (n=21) are given a lateral cerebral ventricle injection of 0.9% normal saline; (2) Rats in the IR group (n=21) are given a lateral cerebral ventricle injection of 0.9% normal saline 30 min before middle cerebral artery occlusion (MCAO); (3) Rats in the Carbenoxolone (CBX) group (n=21) are given a lateral cerebral ventricle injection of CBX (5 μg/mL×10 μL) 30 min before MCAO; (4) Rats in the Diazoxide (DZX) group (n=21) are given a lateral cerebral ventricle injection of DZX (2 mM×30 μL) 30 min prior to MCAO; (5) Rats in the 5-HD group (n=21) are given a lateral cerebral ventricle injection of 5-HD (100 mM×10 μL), and after 10 min, DZX is injected 15 min prior to MCAO; (6) The rats in the DZX + Ro group (n=15) are given a lateral cerebral ventricle injection of DZX, and after 10 min, Ro-31-8425 (400 μg/kg) is injected 15 min prior to MCAO; (7) The rats in the 5-HD+PMA group (n=15) are given an intraperitoneal injection of PMA (200 μg/kg) after the injection of 5-HD and DZX.
References	[1]. Xu F, et al. Protein kinase C-mediated Ca2+ entry in HEK 293 cells transiently expressing human TRPV4. Br J Pharmacol. 2003 Sep;140(2):413-21. [2]. Mugami S, et al. Differential roles of PKC isoforms (PKCs) and Ca2+ in GnRH and phorbol 12-myristate 13-acetate (PMA) stimulation of p38MAPK phosphorylation in immortalized gonadotrope cells. Mol Cell Endocrinol. 2017 Jan 5;439:141-154. [3]. Hou S, et al. Mechanism of Mitochondrial Connexin43's Protection of the Neurovascular Unit under Acute Cerebral Ischemia-Reperfusion Injury. Int J Mol Sci. 2016 May 5;17(5). pii: E679. [4]. Zhang T, et al. MPTP-Induced Dopamine Depletion in Basolateral Amygdala via Decrease of D2R Activation Suppresses GABAA Receptors Expression and LTD Induction Leading to Anxiety-Like Behaviors. Front Mol Neurosci. 2017 Aug 7;10:247.

Density	1.2±0.1 g/cm3
Boiling Point	698.1±55.0 °C at 760 mmHg
Molecular Formula	C₃₆H₅₆O₈
Molecular Weight	616.825
Flash Point	208.1±25.0 °C
Exact Mass	616.397522
PSA	130.36000
LogP	7.71
Vapour Pressure	0.0±5.0 mmHg at 25°C
Index of Refraction	1.553
Water Solubility	DMSO: DMSO solutions can be stored dark at −20?#x00b0;C for at least six months.soluble

Name:	Phorbol 12-myristate 13-acetate 99% Material Safety Data Sheet
Synonym:	PMA; TPA; 12-O-Tetradecanoylphorbol 13-acetat
CAS:	16561-29-8

Section 1 - Chemical Product MSDS Name:Phorbol 12-myristate 13-acetate 99% Material Safety Data Sheet
Synonym:PMA; TPA; 12-O-Tetradecanoylphorbol 13-acetat

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16561-29-8	Phorbol 12-myristate 13-acetate	99%	unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25

Section 3 - HAZARDS IDENTIFICATION

EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.Cancer suspect agent.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
Toxic in contact with skin.
Ingestion:
Poison by ingestion.
Inhalation:
Toxic if inhaled.
Chronic:
Not available.

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Deep freeze (below -20C).

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16561-29-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: colorless to white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Not available.
Specific Gravity/Density:
Molecular Formula: C36H56O8
Molecular Weight: 616.3872

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, light, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16561-29-8: QH4377000 LD50/LC50:
Not available.
Carcinogenicity:
Phorbol 12-myristate 13-acetate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 16561-29-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16561-29-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16561-29-8 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A

Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi: Irritant;
Risk Phrases	R38
Safety Phrases	S36/37
RIDADR	2928
WGK Germany	3
RTECS	QH4377000
Packaging Group	II
Hazard Class	6.1(a)

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4β-Phorbol 12-myristate 13-acetate

Tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester

TPA

PMA

12-O-Tetradecanoylphorbol-13-acetate

tetradecanoylphorbol acetate

MFCD00036736

phorbol 13-acetate 12-myristate

(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-Acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate

12-O-Tetradecanoylphorbol 13-acetate

4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate

(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate

Phorbol 12-myristate 13-acetate