Menthyl acetate

Details

• Internal ID: b09775bf-e5ae-4448-b7c4-214bef1c05df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (5-methyl-2-propan-2-ylcyclohexyl) acetate
• SMILES (Canonical): CC1CCC(C(C1)OC(=O)C)C(C)C
• SMILES (Isomeric): CC1CCC(C(C1)OC(=O)C)C(C)C
• InChI: InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3
• InChI Key: XHXUANMFYXWVNG-UHFFFAOYSA-N
• Popularity: 428 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.30 g/mol
• Exact Mass: 198.161979940 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 16409-45-3
• Menthol, acetate
• Menthyl acetate racemic
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate
• Acetic acid, p-menth-3-yl ester, dl-
• DTXSID20859153
• RefChem:1088940
• DTXCID30210413
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1alpha,2beta,5alpha)-
• 201-911-8
• 240-459-6
• 249-409-8
• LF3LEI45OH
• 89-48-5
• 29066-34-0
• 2230-87-7
• (5-methyl-2-propan-2-ylcyclohexyl) acetate
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-rel-
• (1R)-(-)-Menthyl acetate
• (2-isopropyl-5-methyl-cyclohexyl) acetate
• 5-Methyl-2-(1-methylethyl)cyclohexanol acetate
• d-Neomenthyl acetate
• 2-Isopropyl-5-methylcyclohexyl acetate
• Neomenthol acetate
• FEMA Number 2668
• L-Menthyl acetate;(-)-Menthyl acetate
• HSDB 824
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-
• (.+/-.)-Menthol acetate
• EINECS 240-459-6
• (1R,2S,5R)-rel-2-Isopropyl-5-methylcyclohexyl acetate
• enthyl acetate
• AI3-36197
• Menthol, neo-
• CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, ACETATE, (1.ALPHA.,2.BETA.,5.ALPHA.)-
• Menthyl Acetate; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate (ACI); Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate (9CI); Menthol, acetate (6CI, 8CI); 2-Isopropyl-5-methylcyclohexyl acetate; Acetic acid 5-methyl-2-(1-methylethyl)cyclohexyl es
• EINECS 218-767-7
• Acetate de menthanyle
• (5R)-2-Isopropyl-5-methylcyclohexyl acetate
• starbld0011430
• Menthyl acetate, 97%
• acetic acid menthyl ester
• 5-methyl-2-(propan-2-yl)cyclohexyl acetate
• [(1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] acetate
• SCHEMBL57396
• CHEMBL254585
• SCHEMBL7732630
• 2-Isopropyl-5-methylcyclohexyl acetate, (1.alpha.,2.beta.,5.alpha.)-
• SCHEMBL10401812
• NSC7350
• Acetic acid, p-menth-3-yl ester
• CHEBI:191550
• HMS5085C03
• NSC-7350
• RAA40945
• DL-Menthyl acetate, >=97%, FG
• L-enthyl acetate;(-)-enthyl acetate
• MSK014185
• NSC122112
• AKOS015837885
• NSC 122112
• NSC-122112
• SB44841
• SB46743
• AS-83629
• DB-063670
• DB-071375
• NS00077576
• Cyclohexanol, acetate, (1.alpha.,2.alpha.,5.beta.)-
• Menthyl acetate, primary pharmaceutical reference standard
• Cyclohexanol, acetate, [1S-(1.alpha.,2.alpha.,5.beta.)]-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1.alpha.,2.beta.,5.alpha.)-(.+/-.)-
• InChI=1/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.8992	89.92%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8305	83.05%
OATP2B1 inhibitior	-	0.8499	84.99%
OATP1B1 inhibitior	+	0.9599	95.99%
OATP1B3 inhibitior	+	0.9650	96.50%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9554	95.54%
P-glycoprotein inhibitior	-	0.9558	95.58%
P-glycoprotein substrate	-	0.8970	89.70%
CYP3A4 substrate	-	0.5165	51.65%
CYP2C9 substrate	+	0.5942	59.42%
CYP2D6 substrate	-	0.8718	87.18%
CYP3A4 inhibition	-	0.9496	94.96%
CYP2C9 inhibition	-	0.9097	90.97%
CYP2C19 inhibition	-	0.8249	82.49%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.8324	83.24%
CYP2C8 inhibition	-	0.9764	97.64%
CYP inhibitory promiscuity	-	0.9652	96.52%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.6467	64.67%
Eye corrosion	+	0.5726	57.26%
Eye irritation	+	0.9082	90.82%
Skin irritation	+	0.5924	59.24%
Skin corrosion	-	0.9815	98.15%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6309	63.09%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.6677	66.77%
skin sensitisation	+	0.6257	62.57%
Respiratory toxicity	-	0.9222	92.22%
Reproductive toxicity	-	0.8444	84.44%
Mitochondrial toxicity	-	1.0000	100.00%
Nephrotoxicity	+	0.6178	61.78%
Acute Oral Toxicity (c)	IV	0.5253	52.53%
Estrogen receptor binding	-	0.8298	82.98%
Androgen receptor binding	-	0.7563	75.63%
Thyroid receptor binding	-	0.6951	69.51%
Glucocorticoid receptor binding	-	0.7958	79.58%
Aromatase binding	-	0.8963	89.63%
PPAR gamma	-	0.9260	92.60%
Honey bee toxicity	-	0.8005	80.05%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7093	70.93%
Fish aquatic toxicity	+	0.9705	97.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.25%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.11%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.91%	97.25%
CHEMBL2581	P07339	Cathepsin D	87.79%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.68%	95.71%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	84.90%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.64%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.46%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.61%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.96%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.15%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.08%	89.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.81%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.73%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.55%	94.80%

Plants that contains it

• Agathosma betulina
• Artemisia scoparia
• Clinopodium pamphylicum
• Cryptomeria japonica
• Descurainia sophia
• Hesperozygis rhododon
• Juniperus oxycedrus
• Lepechinia chilensis
• Mentha × piperita
• Mentha × verticillata
• Mentha arvensis
• Mentha canadensis
• Minthostachys mollis
• Origanum cordifolium
• Platostoma africanum
• Polygala senega
• Senna alexandrina
• Thapsia villosa
• Vanilla planifolia

Cross-Links

• PubChem: 27867
• NPASS: NPC274261
• LOTUS: LTS0207854
• wikiData: Q72488412