(-)-Bornyl acetate (L-(-)-Bornyl acetate) is a less active isomer of (+)-Bornyl acetate found in hyssop oil. (-)-Bornyl acetate has antifungal activity.

Physicochemical Properties

Molecular Formula	C12H20O2
Molecular Weight	196.29
Exact Mass	196.146
CAS #	5655-61-8
Related CAS #	Bornyl acetate;76-49-3;(+)-Bornyl acetate;20347-65-3
PubChem CID	6448
Appearance	Colorless to light yellow liquid
Density	1.0±0.1 g/cm3
Boiling Point	223.5±0.0 °C at 760 mmHg
Melting Point	29ºC
Flash Point	84.4±0.0 °C
Vapour Pressure	0.1±0.4 mmHg at 25°C
Index of Refraction	1.480
LogP	3.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	14
Complexity	270
Defined Atom Stereocenter Count	0
SMILES	CC(=O)O[C+]12(C)C(C)(C)CCC(C2)C1
InChi Key	KGEKLUUHTZCSIP-UHFFFAOYSA-N
InChi Code	InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3
Chemical Name	(1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl) acetate
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
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Human Endogenous Metabolite
ln Vitro	In comparison to seedlings exposed to ()-bornyl acetate, the wavy roots of the former have a considerable lengthening[1]. When separately administered to barley seedlings, (-)-Bornyl acetate (L-bornyl acetate) decreased powdery mildew infection in comparison to ether-free controls[2].
ADME/Pharmacokinetics	Absorption, Distribution and Excretion The percutaneous absorptions of camphene, isoborneol-acetate, limonene, menthol and alpha-pinene as constituents of a foam bath (Pinimenthol) were measured on animals using radioactively labelled ingredients. Pharmacokinetic measurements showed maximum blood levels for all tested ingredients 10 min after the onset of percutaneous absorption. None of the ingredients was preferentially absorbed. Blood levels of all ingredients after 10 min of percutaneous absorption were a direct function of the size of the skin area involved. Metabolism / Metabolites Isobornyl acetate readily hydrolyzes (within hours) to isobornyl alcohol during the first step of its biochemical pathway. The alcohol will become conjugated with glucoronic acid and be excreted in the urine (expected within hours to days).
Toxicity/Toxicokinetics	Toxicity Summary IDENTIFICATION AND USE: Isobornyl acetate is used in soaps, detergents, creams and lotions and perfumes. HUMAN STUDIES: A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 10% and produced no sensitization reactions. ANIMAL STUDIES: Isobornyl acetate applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was mildly irritating. Isobornyl acetate was administered daily to rats in doses of 0, 15, 90 or 270 mg/kg bw for 13 wk. Male rats had signs of nephrotoxicity at 90 mg/kg and 270 mg/kg/day, as well as signs of hepatotoxicity at 270 mg/kg. Isobornyl acetate was investigated in a 1-generation reproduction study in rats and it did not produce developmental toxicity. Increased incidences of excess salivation occurred in parent generation male and female rats at 100 and/or 300 mg/kg/d throughout the dosage period, and low incidences of urine-stained abdominal fur were seen in females at 300 mg/kg/d during the gestation period. Non-Human Toxicity Values LD50 Rabbit dermal >20 g/kg LD50 Rats oral >10 g/kg LD50 Mice oral 3100 mg/kg LD50 Rat oral 9050 mg/kg
References	[1]. Exposing Arabidopsis seedlings to borneol and bornyl acetate affects root growth: Specificity due to the chemical and optical structures of the compounds. Journal of Plant Interactions Volume 2, 2007 - Issue 2. [2]. Antifungal Activity of the Essential Oil of Hyssop (Hyssopus offcinalis). J. Phytopathology 149, 673±678 (2001).
Additional Infomation	Bornyl acetate has been reported in Artemisia thuscula, Curcuma xanthorrhiza, and other organisms with data available. Mechanism of Action A possible explanation for the nephrotoxic effects in males but not females is the accumulation of alpha-2u-globulin, a protein in the male rat kidney that appears to lead to renal tubule tumor formation.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (509.45 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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. Solubility in Formulation 2: 2.5 mg/mL (12.74 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.0945 mL	25.4725 mL	50.9450 mL
	5 mM	1.0189 mL	5.0945 mL	10.1890 mL
	10 mM	0.5095 mL	2.5473 mL	5.0945 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.