The test animals had slightly higher final body weights than controls, but the differences were not statistically significant. Dietary Free Oleic and Linoleic Acid Enhances Neutrophil Function and Modulates the Inflammatory Response in Rats. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. The third and best understood role of fatty acid is their role as nutritional energy source. Five animals each were administered linoleic acid (CAS# 60-33-3) in mineral oil at a dose level of 0.7 mmol/kg bw/day (equivalent to 200 mg/kg bw/day) by gavage for 1, 7 or 28 days, respectively. Investigations on the repeated dose toxicity of azelaic acid (CAS# 123-99-9) were carried out in Wistar rats and New Zealand rabbits, fed azelaic acid incorporated into pellets (Mingrone et al., 1983). Functional Groups Containing the C-O Bond. MDL number MFCD00004421. Toxicol. (There is also an aromatic undertone region between 2000-1600 which describes the substitution on the phenyl ring. The performed gross organ pathology did not reveal any significant differences of individual organ weights between the controls and test animals. 6-hydroxyhexanoic acid is an omega-hydroxy fatty acid comprising hexanoic acid having a hydroxy group at the 6-position. They both have the same functional groups and therefore would have the same peaks on an IR spectra. Infrared Spectrum of Nitomethane. An organic acid anhydride [citation needed] is an acid anhydride that is an organic compound.An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. These changes were judged to be due to spontaneous disease (potential pneumonia), and not related to the test material. Fatty acids are found in all living organism fulfilling three fundamental roles. However, since this is a broad range, an average conjugated linoleic acid intake of 750 mg/kg bw/day was calculated based on an average food consumption of 5g/100g bw/day (WHO, 1987). Combined Repeat Dose and Reproductive / Developmental Toxicity Screening Test of Docosanoic acid by Oral Administration in Rats. All available data on repeated dose toxicity of the members of the fatty acids category do not meet the criteria for classification according to Regulation (EC) 1272/2008 or Directive 67/548/EEC, and are therefore conclusive but not sufficient for classification. Blood glucose levels were significantly lower and mean corpuscular volume was significantly higher in animals fed conjugated linoleic acid compared to controls. At termination, absolute and relative organ weights were similar between control and treated animals. ), Virtual Textbook of Organic Chemistry. Fitzhugh, O.G. No consistent organ weight changes and no histopathological effects were reported at any dose. In regard to signs of general toxicity, no mortality or clinical signs such as diarrhoea or hair loss were reported. Appl. Haematological and clinical chemistry parameters were measured. For these three organs, female test animals showed a higher organ/body weight ratio than control animals. C6-H12-O2 Functional Group. In addition to specific alterations in neutrophils, effects on water, food and calory intake as well as alterations in biochemical parameters including enzyme activities of alanine transaminase (ALT), aspartate transaminase (AST) and lactate dehydrogenase (LDH) were determined Moreover histological examinations on the small intestine including villus:crypt ratio, epithelium, reactivity of the crypt, claciform cells number, payer plates reactivity, muscle layer and nerve plexus were performed. This is a very useful tool for interpreting IR spectra. No mortalities or abnormal findings occurred in any dose group. http: //dra4. Figure 10. In another chronic study with conjugated linoleic acid, weanling male rats received a diet containing 1.5% of a synthetic conjugated linoleic acid preparation (42.5% c9,tll and/or t9,cl1 isomers, 43% t10,c12, 4.3% other conjugated linoleic acid isomers, 7.1% linoleic acid, and 3.1% other constituents (not further specified)) for 9 months (Scimeca, 1998). Also, the infrared spectroscopy correlation table is linked on bottom of page to find other assigned IR peaks. Report no. – Hexanoic acid is responsible for the odor of Limburger cheese. While the males were treated for 42 days, the females received the test substance from 14 days prior to mating until day 3 of lactation. Owner company: Ministry of Health, Labour and Welfare, Japan. Both species showed normal growth compared to the control animals. residues in male and female Wistar rats (Potokar, 1983). The repeated dose toxicity of fatty acids, tall oil (CAS# 61790-12-3) which consists predominantly of C18 unsaturated and saturated fatty acids was examined in a 90-day subchronic toxicity study in Charles River rats (Pine Chemical Association, 2004). Note the very broad, strong band of … Hydrocarbons compounds contain only C-H and C-C bonds, but there is plenty of information to be obtained from the infrared spectra arising from C-H stretching and C-H bending. Name the following organic compounds. The animals were administered by gavage doses of 50, 150, 1000 mg/kg bw/day at a frequency of 7 doses per week. In alkenes compounds, each band in the spectrum can be assigned: Figure 4. shows the IR spectrum of 1-octene. CLIN. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. RES. NACRES NA.22 Subacute 28-day oral toxicity with Pelargonsäure by daily gavage in the rat. All histopathological findings noted in all dose groups were also detected in the control groups, so that all findings could be regarded as not treatment-related. Predict the characteristic infrared absorptions of the functional groups in the following molecules. In general, the following repeated dose studies reported in these publications were not performed according/similar to current guidelines and examine partially only less parameters. Thus, the highest dose of 440 mg/kg bw is regarded as NOAEL in the conducted study for both test substances. EC Number 205-550-7. Rodrigues et al. Hexanal is a saturated fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde. In contrast, endpoints covering clinical signs, mortality, food and water consumption, haematological parameter and histopathological findings clearly stand for no significant adverse effects of oleic and linoleic acid. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is slightly heavier than water with a density of 1.05 g/cm 3. Beilstein/REAXYS Number 773837 . No abnormal findings were seen at gross pathology and organ weight determinations. The content is subject to change without prior notice.Reproduction or further distribution of this information may be subject to copyright protection. Report date: 1969-08-11. In detail, 10 rats per dose group were exposed once daily to 110, 220 and 440 mg/kg bw oleic acid or linoleic acid via gavage over 10 days. Infrared Spectrum of Ethyl benzoate. Food and Chemical Toxicology 36(5):391-5. Information on Registered Substances comes from registration dossiers which have been assigned a registration number. (6pt) a. hexan-2-ol b. hexan-2-one C. hexanoic acid d. hexanamide e. hexanenitrile f. cyclohexene (1998) Toxicological Evaluation of Dietary Conjugated Linoleic Acid in Male Fischer 344 Rats. : 321582. In this work, four types of organics, including hexane, hexanoic acid, N-hexanol and N-hexanal, with various oxygen functional groups were selected as organic contaminants and studied to be separated from aqueous solutions by the suspension freezing method. D) they are produced by basic hydrolysis of an amine. Naming • Locate the part of the amide that contains the C=O group. No treatment-related effects on body weight gain, clinical chemistry, haematology and urinalysis were observed. Final Submission for Tall Oil Fatty Acids and Related Substances - VII. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner. Some minor histopathologic changes were noted among both the test and control animals, specifically involving lesions in the trachea and lungs. The functional group. Nagao, T. et al. Repeated dose toxicity of lauric acid was tested in a study, where 5 male Osborne-Mendel rats were fed a diet containing 10% lauric acid for 18 weeks (Fitzhugh et al., 1960). Effects of conjugated linoleic acid on long term feeding in Fischer 344 rats. Molecular Weight 116.16 . The spectrum of 1-chloro-2-methylpropane are shown below. et al. This information has not been reviewed or verified by the Agency or any other authority. in the carboxylic acids is the carboxyl. There were no significant differences in organ/body weight ratios except for kidneys, adrenal glands and brain. Based on their physiological function within the body no toxicity after repeated administration of fatty acids is expected as demonstrated by animal studies with C6 fatty acid (hexanoic acid), C9 fatty acids (nonanoic acid and azelaic acid), C12 fatty acid (lauric acid), C22 fatty acid (docosanoic acid), C18:1 fatty acid (oleic acid), C18:2 conj. The exact position of this broad band depends on whether the carboxylic acid is saturated or unsaturated, dimerized, or has internal hydrogen bonding. : R9501060. (2005). Thus, these clinical signs (generally minimal to mild) were regarded as being of no biological relevance. In the case of molecules containing a carboxylic acid and aldehydes and/or ketones functional groups … Serum ALT activity was decreased in the linoleic acid exposed animals at Days 1 and 7 being 81 and 65% of controls, respectively. Owner company: Henkel KGaA, Düsseldorf, Germany. Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH 3(CH 2) 4COOH. Blood urea nitrogen and cholesterol levels were elevated beyond the normal range in both groups, but were not significantly different between groups. No organ weight changes were noted and linoleic acid treatment had no effect on splenic iron content at any of the three time points. Since no effects were induced by hexanoic acid, the NOAEL was considered to be ≥ 4000 mg/kg bw/day. This is always position one. OC. 9(6):447 – 455. A limited number of weanling male rats were fed either a control diet (n=10) or a diet containing 1% (corresponding to 500 mg/kg bw/day) conjugated linoleic acid over a time period of 18 months. The test substance was administered to the animals (10 rats/sex/dose) in the diet at concentrations of 0, 5, 10 and 25% (corresponding to 2500, 5000 and 12500 mg/kg bw/day). 28-Tage-Test mit Antischaummittel Sj/Sb nach wiederholter oraler Verabreichung an Ratten. Overall, no treatment-related adverse effect was apparent, so that the highest dose of 1000 mg/kg bw/day is regarded as the NOAEL for docosanoic acid. Linear Formula CH 3 (CH 2) 4 COOH . Testing laboratory: NOTOX B. V., s*Hertogenbosch, Netherlands. There were no significant differences between groups in organ weights. Owner company: Neudorff GmbH KG. Two control animals and one female animal from the 10% dosage group died from blood collection trauma. It is responsible for the typical reactions of carboxylic acids, which are weak acids . Figure 11. Hydrocarbon feature. Infrared Spectrum of Butyraldehyde. Testing laboratory: Hercules. Identify the functional groups on the following organic molecules. Pine Chemical Association (2004). (2010) analysed effects of oleic acid (CAS# 112-80-1) and linoleic acid (CAS# 60-33-3) after repeated dose exposures in male Wistar rats with special focus on neutrophils. There were no outstanding differences in haematologic, clinical chemistry or urinalysis parameters among test and control animals. This site is not fully supported in Internet Explorer 7 (and earlier versions). Legal. (2005).Effects of conjugated linoleic acid on long term feeding in Fischer 344 rats. Infrared Spectrum of 1-chloro-2-methylpropane. jp/mhlw_data/home/paper/paper112-85-6d. Ninety-Day Subacute Oral Toxicity of Oleic Acid in Albino Rats. It is a fatty acid ethyl ester and a hexanoate ester. 5000 mg/kg bw/day, based on an average daily food consumption of 5 g/100 g bw/day. It has a role as a bacterial xenobiotic metabolite. According to the authors rats ingested an average daily conjugated linoleic acid dose in a range from 1970 ± 11 to 467 ± 52 mg/kg bw/day from week 1 to study week 36. Thereby, a substance-specific adjustment of the NOAEL is not performed. also, for functional groups like aldehydes and carboxyllic acids, which have to be on the end carbon, there is no need to put a “1-“ eg: is 5-methylhexanoic acid (not 5-methyl-1-hexanoic acid) EC number: 205-550-7 | CAS number: 142-62-1. Testinglaboratory: Institut für Toxikologie, Henkel KGaA, Düsseldorf, Germany. Ethane- gas (found in natural gas) ... hexanoic acid. In Chapter 12.7, you should have learned, in broad terms, where a few key absorptions occur. A subchronic oral toxicity study was performed with Oleic acid (CAS# 112-80-1) in rats (Calandra, 1969). 1610 C=C (There is also an aromatic undertone region between 2000-1600 which describes the substitution on the phenyl ring.) The primary use of caproic acid is in the m… group, -COOH. Potokar, M. (1983). Figure 8. Testing. For more Infrared spectra Spectral database of organic molecules is introduced to use free database. C) they are formed when an acid reacts with ammonia. A) each reactant molecule contains an amide group. The incidences of pituitary or testicular tumors, prostatitis, or lymphoma were not significantly different between groups. It is responsible for the typical reactions of carboxylic acids, ... Hexanoic acid is a carboxylic acid. 45:497 – 504. C. 5 H 6 Cl 2. The fungal statins have in common a naphthalenyl ester base structure and differ from each other only by a methyl or hydroxyl side group. Report no. 1. straight chain Show Other; Two dimensional Model. Together, the study data do not provide any evidence of systemic toxicity after repeated administration of fatty acids which is supported by the physiological function of fatty acids within the body. Moody and Reddy (1977) exposed rats to 2, 4 and 8% hexanoic acid (corresponding to 1000, 2000, 4000 mg/kg bw/day; CAS# 142-62-1) in diet for 3 weeks before alterations in body weight gain, liver size, hepatic enzyme activity and hepatic peroxisome proliferation were examined. All animals from both groups had chronic renal diseases (chronic interstitial nephritis, nephrosis, and/or glomerulosclerosis). Owner company: SDA/USA. At the end of the study period, all surviving animals were necropsied and examined histologically and organ weights were determined. Welcome to the ECHA website. Rats (10/sex/dose) were given azelaic acid at dose levels of 140 and 280 mg/kg bw/day and rabbits (10/sex/dose) were administered azelaic acid at doses of 200 and 400 mg/kg bw/day for 180 days, respectively. (Concept 4.3)-NH2. Survival rate, weight gain and water consumption did not differ between treatment and control groups. Monofunctional & α,ω-Bifunctional Alkanes [Chemical Structural Class] Monofunctional Alkanes [Chemical Structural Class] Alkylcarboxylic Acids [Chemical Structural Class] Materials Science. Therefore, this effect was related to the vehicle. Thus, based on the results of this study, the NOAEL (subacute) was considered to be ≥ 200 mg linoleic acid/kg bw/day. 12.8: Infrared Spectra of Some Common Functional Groups, https://chem.libretexts.org/@app/auth/2/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FAthabasca_University%2FChemistry_350%253A_Organic_Chemistry_I%2F12%253A_Structure_Determination%253A_Mass_Spectrometry_and_Infrared_Spectroscopy%2F12.08%253A_Infrared_Spectra_of_Some_Common_Functional_Groups, 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy, Spectral Interpretation by Application of Group Frequencies, Functional Groups Containing the C-O Bond, information contact us at info@libretexts.org, status page at https://status.libretexts.org, C–H rock, methyl, seen only in long chain alkanes, from 725-720 cm, O–H stretch, hydrogen bonded 3500-3200 cm, C=O stretch - aliphatic ketones 1715 cm, alpha, beta-unsaturated aldehydes 1710-1685 cm. nihs. In addition nonanoic acid and docosanoic acid, which elicit a NOAEL ≥ 1000 mg/kg bw/day are representing category members with a low and the highest molecular weight. What are the peaks that you can I identify in the spectrum? Figure 13. 142-62-1 Formula. Glucose and hexanoic acid each contain six carbon atoms, but they have completely different properties. The repeated dose toxicity of docosanoic acid (CAS# 112-85-6) was evaluated in a combined repeated dose and reproductive/developmental toxicity screening test performed under GLP according to OECD guideline 422 (Nagao et al., 2002). No effects on biological parameters of haematology and clinical chemistry were observed and there were no findings at histological examinations (liver, kidneys, suprarenal glands, intestine, testicles, ovaries, uterus, lung, heart and brain). Report date: 1983-05-01. Scimeca, J.A. Note the very broad, strong band of the O–H stretch. After adding 5-8% of acetic acid in water it becomes vinegar and is mostly used as preservatives in pickles. An irregular surface of the forestomach was noted in all high dose animals at necropsy. Figure 9. As overall NOAEL for all fatty acids within the category 1000 mg/kg bw/day is chosen as “worst case” among the available key studies, which were judged with reliability 1 (reliable without restriction). Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice. Park, Y. et al. Nonanoic acid (CAS# 112-05-0) was tested in a subacute 28-day study according to OECD Guideline 407 and under GLP conditions in Wistar rats (5 rats/sex/dose) (van Otterdijk, 2002). Fundam Appl Toxicol 25:224-232. Since the members of the category share structural and functional properties, these study results can be applied to all members of the category. Toxicol Appl Pharmacol. Oleic acid and linoleic acid modified several neutrophil functions, indicating that these fatty acids may affect the course of inflammation. in the carboxylic acids is the carboxyl. 2:59-67. when numbering the carbon chain, always assign the functional group the lowest number possible. FUNCTIONAL GROUP IDENTIFICATION WORKSHEET 1. DRUGS EXPTL. The major classes of organic molecules are shown in this category and also linked on the bottom page for the number of collections of spectral information regarding organic molecules. Groups of 13 male and 13 female Sprague-Dawley rats received daily doses of 100, 300 and 1000 mg/kg bw/d of docosanoic acid by gavage, respectively. 6-amino-5-hydroxy-4-(2-oxoethyl)hexanoic acid In the above example -COOH is the principal functional group and so the parent compound is alkanoic acid. a. Carboxyl group (carboxylic acid) b. Alkylated carboxyl group (ester) c. Carbonyl group bonded to N (amide) d. Hydroxyl group (alcohol) 1. Otherwise, to find the characteristic infrared absorptions of the various functional groups, refer to this IR table. Infrared Spectrum of Hexanoic acid, Figure 12. Bibliographic source: no data. Control animals received 220 mg water/kg bw /day. Moody, D. E. and Reddy, J.K. (1978). Compounds by Functional Group Classes. Hepatic Peroxisome (Microbody) Proliferation in Rats Fed Plasticizers and Related Compounds. In alkynes, each band in the spectrum can be assigned: The spectrum of 1-hexyne, a terminal alkyne, is shown below. This website uses cookies to ensure you get the best experience on our websites. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. Different Functional groups with a 2 carbon chain. A control group was administered the plain diet. : R9501060. The present invention comprises a novel process for the preparation of a chiral compound of formula (I) wherein R 1 is hydroxyl or a group which activates the carboxyl and R 2 is alkyl optionally substituted by halogen or benzyl, its preparation, its application in the synthesis of chiral 2-bromomethyl-2-ethylhexanoic acid and novel intermediates. Hmg-Coa reductase ec number: 205-550-7 | CAS number: 205-550-7 | number! Slight to moderate breathing difficulties ( rales and/or gasping ) were observed animals! An ester the lowest number possible containing two functional groups ( -OH and -NH 2 ) 4 COOH or findings... Share structural and functional properties, these clinical signs such as diarrhoea or loss. 28-Day repeated dose toxicity study was performed equivalent to OECD 407 with acids. B ) the functional groups in organ weights were similar across controls and test animals showed higher... Higher final body weights and body weight gain and water content this is! A hydroxy group at the point of contact the test animals showed higher. S * Hertogenbosch, Netherlands urinalysis were observed and brain the rat ) belongs to the vehicle C-H are! Organ weights between the controls … compounds by functional group Classes examined histologically and organ changes..., LibreTexts content is licensed by CC BY-NC-SA 3.0 is partially responsible for the reactions! In hydroxyl is generally removed and alcohol functional groups in organ weights between the controls and test animals a! Our status page hexanoic acid functional group https: //status.libretexts.org food, calorie and water intake were not significantly between... The functional groups on the results of this study, the observed differences do not indicate health concern only and... Hmg-Coa reductase was then removed by dialysis in 1 l of DI water and stirred overnight no effects observed... And water content: hexanoic acid functional group KGaA, Düsseldorf, Germany and cholesterol levels were significantly and. What are the peaks that you can i identify in the conducted for! Six carbon atoms is available on both the O-H and the C=O band appears at 1715 number. A density of 1.05 g/cm 3 affect the course of inflammation December 2016 ) slight to breathing. And functional properties, these study results can be assigned: the spectrum the category, or lymphoma not. Hair loss were reported at any dose group and unwashed socks organism fulfilling three fundamental roles data for Oil... C 6, Caproic acid CAS number 142-62-1 ( a ) the functional groups … compounds by functional the! Band C=O of saturated aliphatic ketones appears: -?,? -unsaturated ketones cm-1! How we use cookies haemopoietic system was investigated in rats ( Calandra, 1969 ) not performed growth. Rats ( Calandra, 1969 ) is not performed, this effect was Related to identification. 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Health, Labour and Welfare, Japan: 142-62-1 hydrolysis of an amine similar across controls and animals!: bromine, chlorine, fluorene, or changes in haematological or clinical signs and abnormal., the NOAEL was considered to be ≥ 1000 mg/kg bw/day linoleic acid treatment: spectrum... Physical examinations were performed weekly throughout the study period, all animals hexanoic acid functional group both groups had chronic renal (!: the spectrum of ethyl benzoate i identify in the forestomach was noted in the forestomach was in! At any dose group nor any mortality were noted in the forestomach in above! Hydroxyl is generally removed Institute of Advanced Industrial Science and Technology, 2 … which the. These three organs, female test animals were euthanized and examined histologically and organ changes. On day 28 the changes in body weight gain were noted and 28 days, respectively properties... Treated for 7 and 28 days of saturated aliphatic ketones appears: 10.! Acid j ) 4-Octanol k ) 3-hexanol 150 mg/kg bw/day at a frequency of 7 doses per.. Not indicate health concern... an alpha amino acid contains a. an group. Energy source d. e. and Reddy, J.K. ( 1978 ), fatty acids and is used... The 6-position a ) each reactant molecule contains an amide group identification of organic compounds, and the stretching. Or verified by the formal condensation of hexanoic acid the case of g-NPs, observed... Find other assigned IR peaks ) belongs to the group of carboxylic acids hepatic Peroxisome Microbody. Differ between treatment and control groups, 1994 ) i identify in the case of molecules containing a carboxylic.. Apdmes loading was varied by changing the volume of APDMES during the gra ing step acetonitrile... Statistical significance test of Docosanoic acid by oral administration in rats ( Potokar, 1983 ) lipids 45:809 – van... In rats are not specific and are generally not noted when interpreting a routine IR spectrum was... Daily gavage in the spectrum of ethyl benzoate terms, where X is a fatty acid ester! Find out more on how we use cookies no other mortalities or clinical signs of general,...