Absorption, Distribution and Excretion
2,4-D BUTYL ESTER ADMIN ORALLY TO RABBITS AT 150 OR 490 MG/KG WAS FOUND IN HIGHEST AMOUNTS IN BLOOD, KIDNEYS, LIVER, SPLEEN, LUNG, HEART, AND URINE DURING FIRST 24 HR AFTER ADMIN.
Leaves absorb nonpolar (ester) forms most readily. ... The esters of 2,4-D tend to resist washing from plants and are rapidly converted to the acid by the plants. ... Following foliar absorption, 2,4-D translocates within the phloem, probably moving with food material. Following root absorption, it may move upward in the transpiration stream. Translocation is influenced by the growth status of the plant. Accumulation of the herbicide occurs principally at the meristematic regions of shoots and roots. /2,4-D/
AFTER SC INJECTION OF 2,4-D & ITS BUTYL & ISOOCTYL ESTERS INTO MICE @ 100 MG/KG, ESTERS WERE ELIM RAPIDLY, & ONLY 5-10% OF THE 2,4-D REMAINED AFTER 1 DAY. ... 2,4-D WAS ELIM IN MILK OF COWS MAINTAINED IN PASTURES TREATED WITH 2,4-D OR ITS BUTYL OR ISOOCTYL ESTER.
/RELATIVE/ RATES OF DISAPPEARANCE FROM PLASMA OF 2,4-D OR ITS BUTYL & ISOOCTYL ESTERS FOLLOWING SINGLE SC INJECTIONS OF 100 MG/KG BODY WT OF COMPOUNDS TO FEMALE C57BL/6 MICE WERE: BUTYL ESTER > ISOOCTYL ESTER > 2,4-D.
For more Absorption, Distribution and Excretion (Complete) data for 2,4-D BUTYL ESTER (6 total), please visit the HSDB record page.

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Metabolism / Metabolites
MEAL FROM CASTOR BEANS CONTAINED AN ESTERASE THAT HYDROLYZED THE BUTYL ESTER OF 2,4-D ...
The metabolic fate of 2,4-dichlorophenoxyacetic acid (2,4-D) n-butyl ester in rats has not been extensively studied. Upon subcutaneous administration of 100 mg/kg dose of 2,4-D butyl ester to four male Wistar rats, urine samples were analyzed by three analytical techniques for the presence of the butyl ester and metabolites. 2,4-D butylester was rapidly hydrolyzed in the body to form 2,4-D acid. 95% of the administered dose was excreted into the urine as the free acid within 48 hr of injection while only a small fraction (5%) was excreted over an additional 48 hr. No amino acid conjugates or the parent 2,4-D butyl ester could be detected in the urine of treated rats. A minor metabolite (< or = 2% of dose) was detected by GC-MS analysis of urine samples. This compound appears to be a side chain metabolite of the 2,4-D butyl ester. Some chemical properties of the metabolite were characterized, and a 2,4-D hydroxyethyl ester structure proposed. The mechanism of formation of this minor metabolite remains unknown.
Plants hydrolyze 2,4-D esters to 2,4-D, which is the active herbicide. ... Further metabolism ... occurs through three mechanisms, namely, side chain degradation, hydroxylation of the aromatic ring, and conjugation with plant constituents. /2,4-D esters/
HERBICIDAL ACTIVITY OF ESTERS, NITRILES, AMINES (&, OF COURSE, SALTS) APPEARS SIMILAR IF NOT IDENTICAL TO PARENT ACID. THIS IS APPARENTLY DUE TO PRESENCE OF HYDROLYTIC ENZYMES IN PLANTS & IN SOIL MICROORGANISMS THAT CONVERT THESE DERIVATIVES TO PARENT ACID. /2,4-D ESTER/
For more Metabolism/Metabolites (Complete) data for 2,4-D BUTYL ESTER (7 total), please visit the HSDB record page.

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Biological Half-Life
THESE HERBICIDES DO NOT ACCUM IN ANIMALS. THEY ARE NOT EXTENSIVELY METAB BUT ARE ACTIVELY EXCRETED INTO THE URINE ... THEIR PLASMA HALF-LIFE IN MAN IS ABOUT 1 DAY. /CHLOROPHENOXY COMPOUNDS/
... In rats orally or intravenously admin, 2,4-D is excreted primarily in the urine with a half-life of approx 2 hr. /SRP: Unspecified salt or ester of 2,4-D/
The hydrolysis half-life of the n-butyl ester of 2,4-D was determined to be 100 hours in neutral water and much less in aqueous soil suspensions. Smith (1976) reported that the n-butyl ester of 2,4-D undergoes almost complete hydrolysis to 2,4-D in less than 24 hours in moist soil. Similar results were reported for the hydrolysis of the n-butyl and isooctyl esters of 2,4,5-T to 2,4,5-T. Esters of 2,4-D were completely hydrolyzed to 2,4-D within 9 days in lake water. Therefore, rates of biological hydrolysis appear to be greater than rates of chemical hydrolysis.

Interactions
IN STATIC BIOASSAYS WITH FINGERLING RAINBOW TROUT, 1 MG/L CARBARYL DECR LC50 OF 2,4-D BUTYL ESTER FROM 30 TO 11 MG/L.
Cutthroat trout (Salmo clarki) were treated with six different paired mixtures of dicamba, picloram, 2,4-D butyl ester, 2,4-D isooctyl ester, and 2,4-D propylene glycol butyl ether ester. Except for 2,4-D isooctyl ester, the LC50's resulting from mixtures of 2,4-D esters and picloram were lower than LC50's of those herbicides tested individually. Dicamba and 2,4-D isooctyl ester were the least toxic individually and mixtures of dicamba or 2,4-D isooctyl ester with the other herbicides tested did not result in increased toxicity. Results reflect the importance of using combination exposures in determining the biological significance of the simultaneous occurrence of more than one herbicide in surface waters.
The aim of this investigation was to determine the contribution made by the different components of herbicide formulations to the overall toxicity of the formulations. Three related herbicide formulations were chosen. The first, Agent Orange, consisted only of the butyl esters of 2,4,5-T and 2,4-D. The second was Agent Orange diluted with diesel fuel and the third formulation tested was a tree and blackberry killer, which consisted of the butyl ester of 2,4,5-T, the ethyl ester of 2,4-D, diesel fuel and two surfactants. The potential toxic effects of these three formulations were evaluated by determining their inhibitory effects on the oxidative functions of submitochondrial particles prepared from beef heart mitochondria. The effective concentration that caused a 50% inhibition of the activities of the submitochondrial particles was determined for all three formulations. When the toxicity of the individual components of these formulations was evaluated, it was established that the so-called 'inert' components i.e. diesel fuel and surfactants contributed approximately 50% of the overall toxicity of the complete formulations. Hence the results confirm the importance of evaluating the toxicity of complete formulations, rather than only focussing on the active components. While cellular and sub-cellular assays cannot account for pharmacokinetic and pharmacodynamic changes that may affect the toxicity of xenobiotics, the sub-mitochondrial particle test is useful as an initial screening assay.

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Non-Human Toxicity Values
LD50 Mouse oral 380 mg/kg
LD50 Rat oral 920 mg/kg
LD50 Chick (M,F) 2000 mg/kg (1350-2960 mg/kg) oral acid equivalent of 1503 mg/kg /From table, 2,4-D butyl esters/
LD50 Rat oral 600 mg/kg
For more Non-Human Toxicity Values (Complete) data for 2,4-D BUTYL ESTER (8 total), please visit the HSDB record page.

[1]. Formulation and food deprivation affects 2,4-D neurobehavioral toxicity in rats. Neurotoxicol Teratol. Sep-Oct 1987;9(5):363-7.

[2]. Isolation and Characterization of 2,4-D Butyl Ester Degrading Acinetobacter sp. ZX02 from a Chinese Ginger Cultivated Soil. J Agric Food Chem. 2017 Aug 30;65(34):7345-7351.

2,4-d, n-butyl ester is a clear colorless to light brown liquid. (NTP, 1992)

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Mechanism of Action
Total alkaloid concentration, percentage water, crude protein, and neutral-detergent fiber in velvet lupine (Lupinus leucophyllus) were monitored for 3 wk following application of herbicides registered or soon to be registered for rangeland use. ... 2,4-D Butyl ester ... killed most velvet lupine plants and caused a subsequent decrease in total alkaloid concentration, crude protein, and water content as the plants desiccated. Herbicides that effectively killed velvet lupine decreased alkaloid levels, thus lowering the potential for increased livestock poisoning.
... /CHLOROPHENOXY CMPD INCL 2,4-D ESTERS/ EXERT THEIR HERBICIDAL ACTION BY ACTING AS GROWTH HORMONES IN PLANTS. /CHLOROPHENOXY COMPOUNDS/
Chlorophenoxy acid derivatives are metabolized via participation of the hepatic microsomal mixed-function oxidase system. Thus, administration of 2,4-D amine salt and its butyl ester ... to rats induced the enzyme system (aminopyrine demethylase ... and aniline hydroxylase ... although the degree of induction was substantially lower than that from phenobarbital. Prolonged administration of 2,4-D amine salt (0.1 LD50) showed cumulative effects reflected by both clinical and biochemical changes. Stimulation of mixed-function oxidase system may be one of the methods for reducing toxicological effects of this type of compounds. /2,4-D butyl ester/
2,4-Dichlorophenoxyacetic butyl ester (2,4-D b.e.) (3.1 mg/egg) was applied on fertile hen eggs before starting the incubation. Chicks hatched from treated eggs showed motor dysfunctions, postural troubles and edematous muscles. The electromyography revealed muscular weakness, prolonged motor distal latency, and myotonia. The biochemical composition of leg and complexus muscles from 1-day-old chicks was determined. A significant diminution (24%) in the glycogen level of leg muscles was produced by the treatment. There was a small increase (15%) in sarcoplasmic proteins from leg muscles and an increase of a 20 kD protein in the myofibrillar proteins from complexus muscles. Even though total lipid content was not changed, 2,4-D b.e. treatment produced a diminution of sterol esters (20%) and phosphatidylcholine (11%) and an increase of phosphatidylserine (61%), triglycerides (37%) and free fatty acids (FFA) (448%) in leg muscles. Increases of phosphatidylethanolamine (16%), sterols (58%) and FFA (267%) were detected in complexus muscles. A remarkable increase (700-1500%) of unsaturated FFA, e.g. oleic, linoleic and arachidonic acids, was observed. Considering the avian embryo lipid metabolism, it is proposed that FFA and triglycerides were accumulated because they could not be metabolized in the mitochondria.

C12H14CL2O3

277.14

276.032

94-80-4

7206

Colorless to light yellow liquid

1.2±0.1 g/cm3

343.9±27.0 °C at 760 mmHg

9ºC

132.0±22.7 °C

0.0±0.8 mmHg at 25°C

1.518

4.25

0

3

7

17

236

0

O=C(COC1C(Cl)=CC(Cl)=CC=1)OCCCC

CCEFMUBVSUDRLG-IDKOKCKLSA-N

InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m0/s1

(4S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

FEMA No. 4656 L-1,2-Epoxylimonene Limonene oxide, (-)-

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)