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α-Phellandrene

CAT: 0804-HY-121615-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-121615-02Size:10 mM - 1 mL
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Description
α-Phellandrene (alpha-Phellandrene) is an orally active monoterpenoid and insecticide. α-Phellandrene can be isolated from plant essential oils. α-Phellandrene induces Apoptosis and Autophagy. α-Phellandrene promotes cAMP signaling pathway and increases NO production. α-Phellandrene has anti-inflammatory and anticancer (sarcoma) activities. α-Phellandrene shows insecticidal activity against Lucilia cuprina L3. α-Phellandrene reduces mechanical hyperalgesia[1][2][3][4][5][6][7][8][9][10][11].
CAS Number
99-83-2
Product Name Alternative
Alpha-Phellandrene
UNSPSC
12352211
Hazard Statement
H226, H302, H315, H319, H334, H335
Target
Apoptosis; Autophagy; Insecticide; NO Synthase
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; Immunology/Inflammation; Others
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/α-phellandrene.html
Concentration
10mM
Purity
86.66
Solubility
DMSO : 200 mg/mL (ultrasonic)
Smiles
CC1=CCC(C=C1)C(C)C
Molecular Formula
C10H16
Molecular Weight
136.23
Precautions
H226, H302, H315, H319, H334, H335
References & Citations
[1]Abdouli I, et al. TiO2 Catalyzed Dihydroxyacetone (DHA) Conversion in Water: Evidence That This Model Reaction Probes Basicity in Addition to Acidity. Molecules. 2022 Nov 24;27 (23) :8172.|[2]Susanto AC, et al. α‑Phellandrene enhances the apoptosis of HT‑29 cells induced by 5‑fluorouracil by modulating the mitochondria‑dependent pathway. Oncol Rep. 2024 Apr;51 (4) :61.|[3]Hsieh SL, et al. Induction of necrosis in human liver tumor cells by α-phellandrene. Nutr Cancer. 2014;66 (6) :970-9.|[4]Lin JJ, et al. α-Phellandrene alters expression of genes associated with DNA damage, cell cycle, and apoptosis in murine leukemia WEHI-3 cells. Anticancer Res. 2014 Aug;34 (8) :4161-80. |[5]Kang W, et al. Activation of cAMP Signaling in Response to α-Phellandrene Promotes Vascular Endothelial Growth Factor Levels and Proliferation in Human Dermal Papilla Cells. Int J Mol Sci. 2022 Aug 11;23 (16) :8959.|[6]Hsieh LC, et al. Induction of α-phellandrene on autophagy in human liver tumor cells. Am J Chin Med. 2015;43 (1) :121-36.|[7]Chaaban A, et al. Insecticide activity of Curcuma longa (leaves) essential oil and its major compound α-phellandrene against Lucilia cuprina larvae (Diptera: Calliphoridae) : Histological and ultrastructural biomarkers assessment. Pestic Biochem Physiol. 2019 Jan;153:17-27.|[8]Lin JJ, et al. Alpha-phellandrene promotes immune responses in normal mice through enhancing macrophage phagocytosis and natural killer cell activities. In Vivo. 2013 Nov-Dec;27 (6) :809-14. |[9]Pinheiro-Neto FR, et al. α-Phellandrene exhibits antinociceptive and tumor-reducing effects in a mouse model of oncologic pain. Toxicol Appl Pharmacol. 2021 May 1;418:115497. |[10]Gonçalves R L G, et al. α-Phellandrene attenuates tissular damage, oxidative stress, and TNF-α levels on acute model ifosfamide-induced hemorrhagic cystitis in mice. Naunyn-Schmiedeberg's Archives of Pharmacology, 2020, 393: 1835-1848.|[11]Siqueira HDS, et al. α-Phellandrene, a cyclic monoterpene, attenuates inflammatory response through neutrophil migration inhibition and mast cell degranulation. Life Sci. 2016 Sep 1;160:27-33.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

alpha-PHELLANDRENE

Alpha-phellandrene is one of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic). It has a role as a volatile oil component, an antimicrobial agent and a plant metabolite. It is a cyclohexadiene and a phellandrene.

CAS Number99-83-2
PubChem CID7460
IUPAC Name2-methyl-5-propan-2-ylcyclohexa-1,3-diene
Molecular FormulaC10H16
Molecular Weight136.23
XLogP3.2
Topological Polar Surface Area0
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Heavy Atom Count10
Formal Charge0
Complexity161
SMILES
CC1=CCC(C=C1)C(C)C
InChI
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3
InChIKey
OGLDWXZKYODSOB-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of alpha-PHELLANDRENE
CAS: 99-83-2
CID: 7460
Formula: C10H16
MW: 136.23
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight136.23
XLogP33.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Exact Mass136.125200510
Monoisotopic Mass136.125200510
Topological Polar Surface Area0 Ų
Heavy Atom Count10
Formal Charge0
Complexity161
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes